NPASS Compound

Structure

CID162694 OpenBabel06191715532D 22 25 0 0 1 0 0 0 0 0999 V2000 -1.2708 3.7213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3412 2.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9345 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9400 2.9781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 21 1 0 0 0 0 3 4 1 0 0 0 0 3 9 2 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 18 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 10 11 1 0 0 0 0 11 17 1 0 0 0 0 12 14 2 0 0 0 0 12 19 1 0 0 0 0 13 4 1 6 0 0 0 13 15 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 15 10 1 6 0 0 0 15 16 1 0 0 0 0 16 9 1 1 0 0 0 16 18 1 0 0 0 0 17 20 2 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	301.13
Volume:	301.338
LogP:	2.339
LogD:	1.782
LogS:	-3.089
# Rotatable Bonds:	1
TPSA:	59.0
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.635
Synthetic Accessibility Score:	4.003
Fsp3:	0.471
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.617
MDCK Permeability:	2.0122804926359095e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.094
Human Intestinal Absorption (HIA):	0.029
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.009

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.995
Plasma Protein Binding (PPB):	73.90283966064453%
Volume Distribution (VD):	1.957
Pgp-substrate:	22.3160400390625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.325
CYP1A2-substrate:	0.776
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.796
CYP2C9-inhibitor:	0.137
CYP2C9-substrate:	0.773
CYP2D6-inhibitor:	0.754
CYP2D6-substrate:	0.852
CYP3A4-inhibitor:	0.251
CYP3A4-substrate:	0.45

ADMET: Excretion

Clearance (CL):	15.117
Half-life (T1/2):	0.71

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.186
Drug-inuced Liver Injury (DILI):	0.233
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.917
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.05
Carcinogencity:	0.921
Eye Corrosion:	0.004
Eye Irritation:	0.023
Respiratory Toxicity:	0.952

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC162694

Natural Product ID:	NPC162694
*Common Name:**	(5Ar,11Bs,11Cs)-9-Hydroxy-10-Methoxy-1-Methyl-2,3,5,5A,11B,11C-Hexahydroisochromeno[3,4-G]Indol-7-One
IUPAC Name:	(5aR,11bS,11cS)-9-hydroxy-10-methoxy-1-methyl-2,3,5,5a,11b,11c-hexahydroisochromeno[3,4-g]indol-7-one
Synonyms:
Standard InCHIKey:	VLDOBKJPRUQEEC-FVQBIDKESA-N
Standard InCHI:	InChI=1S/C17H19NO4/c1-18-6-5-9-3-4-13-15(16(9)18)10-8-14(21-2)12(19)7-11(10)17(20)22-13/h3,7-8,13,15-16,19H,4-6H2,1-2H3/p+1/t13-,15-,16-/m1/s1
SMILES:	C[NH+]1CCC2=CC[C@@H]3[C@@H](c4cc(c(cc4C(=O)O3)O)OC)[C@H]12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1979251
PubChem CID:	388787
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001775] Amaryllidaceae alkaloids [CHEMONTID:0004122] Homolycorine-type amaryllidaceae alkaloids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26604	Aralia subcapitata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO272	Pittosporum eugenioides	Species	Pittosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26604	Aralia subcapitata	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26154	Erythropodium caribaeorum	Species	Anthothelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26641	Pteroxygonum giraldii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13480	Stereocaulon dactylophyllum	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	54

Activity Type	# Activity
Cell Line	54

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	25003.45	nM	PMID[450023]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC162694 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	1063
0.2-0.3	3423
0.3-0.4	9038
0.4-0.5	9023
0.5-0.6	7146
0.6-0.7	11403
0.7-0.8	1294
0.8-0.85	39
0.85-0.9	11
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9581	High Similarity	NPC35680
0.9429	High Similarity	NPC33256
0.9205	High Similarity	NPC94499
0.8876	High Similarity	NPC35345
0.8865	High Similarity	NPC80472
0.8715	High Similarity	NPC141440
0.8703	High Similarity	NPC286135
0.8453	Intermediate Similarity	NPC230098
0.838	Intermediate Similarity	NPC474745
0.8372	Intermediate Similarity	NPC4304
0.8324	Intermediate Similarity	NPC474325
0.8268	Intermediate Similarity	NPC237044
0.8266	Intermediate Similarity	NPC205167
0.8266	Intermediate Similarity	NPC249274
0.8266	Intermediate Similarity	NPC26353
0.8242	Intermediate Similarity	NPC475981
0.8242	Intermediate Similarity	NPC474746
0.8212	Intermediate Similarity	NPC304675
0.8211	Intermediate Similarity	NPC97086
0.8146	Intermediate Similarity	NPC474708
0.8132	Intermediate Similarity	NPC298339
0.8132	Intermediate Similarity	NPC473562
0.8122	Intermediate Similarity	NPC329816
0.8115	Intermediate Similarity	NPC67346
0.8115	Intermediate Similarity	NPC243483
0.8115	Intermediate Similarity	NPC232533
0.8101	Intermediate Similarity	NPC227683
0.809	Intermediate Similarity	NPC475845
0.8083	Intermediate Similarity	NPC476500
0.8077	Intermediate Similarity	NPC32154
0.8059	Intermediate Similarity	NPC469540
0.8059	Intermediate Similarity	NPC469539
0.8034	Intermediate Similarity	NPC57812
0.8034	Intermediate Similarity	NPC474324
0.8021	Intermediate Similarity	NPC43069
0.8021	Intermediate Similarity	NPC196231
0.8021	Intermediate Similarity	NPC140577
0.8	Intermediate Similarity	NPC214629
0.7969	Intermediate Similarity	NPC64576
0.7969	Intermediate Similarity	NPC201055
0.7969	Intermediate Similarity	NPC254045
0.7969	Intermediate Similarity	NPC151470
0.7969	Intermediate Similarity	NPC311781
0.7967	Intermediate Similarity	NPC241704
0.7958	Intermediate Similarity	NPC267414
0.7956	Intermediate Similarity	NPC329992
0.7955	Intermediate Similarity	NPC135006
0.7946	Intermediate Similarity	NPC475566
0.7933	Intermediate Similarity	NPC181653
0.7933	Intermediate Similarity	NPC190332
0.7926	Intermediate Similarity	NPC226708
0.7906	Intermediate Similarity	NPC14622
0.7906	Intermediate Similarity	NPC70290
0.7906	Intermediate Similarity	NPC46744
0.7906	Intermediate Similarity	NPC73020
0.7906	Intermediate Similarity	NPC124302
0.7906	Intermediate Similarity	NPC215098
0.7874	Intermediate Similarity	NPC267091
0.7853	Intermediate Similarity	NPC24228
0.7853	Intermediate Similarity	NPC204580
0.7835	Intermediate Similarity	NPC119818
0.7835	Intermediate Similarity	NPC202771
0.7835	Intermediate Similarity	NPC328700
0.7835	Intermediate Similarity	NPC2173
0.7833	Intermediate Similarity	NPC100566
0.7833	Intermediate Similarity	NPC100420
0.7824	Intermediate Similarity	NPC72788
0.7824	Intermediate Similarity	NPC226652
0.7824	Intermediate Similarity	NPC120671
0.7824	Intermediate Similarity	NPC314100
0.7821	Intermediate Similarity	NPC180306
0.7816	Intermediate Similarity	NPC243891
0.7812	Intermediate Similarity	NPC83019
0.7807	Intermediate Similarity	NPC18306
0.7806	Intermediate Similarity	NPC126211
0.7801	Intermediate Similarity	NPC174783
0.7797	Intermediate Similarity	NPC150227
0.7784	Intermediate Similarity	NPC147091
0.7778	Intermediate Similarity	NPC124657
0.7778	Intermediate Similarity	NPC474858
0.7772	Intermediate Similarity	NPC474470
0.7772	Intermediate Similarity	NPC207239
0.7766	Intermediate Similarity	NPC157958
0.7765	Intermediate Similarity	NPC320104
0.7765	Intermediate Similarity	NPC218614
0.776	Intermediate Similarity	NPC66909
0.7753	Intermediate Similarity	NPC226428
0.7753	Intermediate Similarity	NPC190020
0.7753	Intermediate Similarity	NPC77679
0.7753	Intermediate Similarity	NPC84935
0.7751	Intermediate Similarity	NPC138438
0.7751	Intermediate Similarity	NPC908
0.7749	Intermediate Similarity	NPC469815
0.7749	Intermediate Similarity	NPC469816
0.7744	Intermediate Similarity	NPC244191
0.7742	Intermediate Similarity	NPC115906
0.774	Intermediate Similarity	NPC199926
0.7737	Intermediate Similarity	NPC319549
0.7735	Intermediate Similarity	NPC252960
0.7725	Intermediate Similarity	NPC166979
0.772	Intermediate Similarity	NPC293624
0.7719	Intermediate Similarity	NPC469615
0.7701	Intermediate Similarity	NPC98809
0.7701	Intermediate Similarity	NPC476394
0.7688	Intermediate Similarity	NPC27887
0.7688	Intermediate Similarity	NPC99179
0.7684	Intermediate Similarity	NPC197188
0.7684	Intermediate Similarity	NPC62051
0.7684	Intermediate Similarity	NPC291510
0.7684	Intermediate Similarity	NPC238672
0.7684	Intermediate Similarity	NPC116850
0.7684	Intermediate Similarity	NPC144801
0.7684	Intermediate Similarity	NPC43872
0.7674	Intermediate Similarity	NPC469683
0.767	Intermediate Similarity	NPC124842
0.7667	Intermediate Similarity	NPC24627
0.7647	Intermediate Similarity	NPC82056
0.7644	Intermediate Similarity	NPC63152
0.764	Intermediate Similarity	NPC16082
0.764	Intermediate Similarity	NPC79998
0.764	Intermediate Similarity	NPC82592
0.7627	Intermediate Similarity	NPC131121
0.7627	Intermediate Similarity	NPC295646
0.7626	Intermediate Similarity	NPC475768
0.7624	Intermediate Similarity	NPC255607
0.7624	Intermediate Similarity	NPC469889
0.7624	Intermediate Similarity	NPC3375
0.7621	Intermediate Similarity	NPC128476
0.7617	Intermediate Similarity	NPC125924
0.7614	Intermediate Similarity	NPC82285
0.7614	Intermediate Similarity	NPC133011
0.7611	Intermediate Similarity	NPC153631
0.7609	Intermediate Similarity	NPC477640
0.7609	Intermediate Similarity	NPC470739
0.7609	Intermediate Similarity	NPC303581
0.7609	Intermediate Similarity	NPC67978
0.7609	Intermediate Similarity	NPC225597
0.7598	Intermediate Similarity	NPC59028
0.7598	Intermediate Similarity	NPC92191
0.7596	Intermediate Similarity	NPC86469
0.7588	Intermediate Similarity	NPC326895
0.7586	Intermediate Similarity	NPC214239
0.7584	Intermediate Similarity	NPC281477
0.7582	Intermediate Similarity	NPC476002
0.7577	Intermediate Similarity	NPC279665
0.7576	Intermediate Similarity	NPC268077
0.7572	Intermediate Similarity	NPC213900
0.7571	Intermediate Similarity	NPC228662
0.7569	Intermediate Similarity	NPC476569
0.7557	Intermediate Similarity	NPC261322
0.7557	Intermediate Similarity	NPC119669
0.7556	Intermediate Similarity	NPC158900
0.7556	Intermediate Similarity	NPC167098
0.7556	Intermediate Similarity	NPC143328
0.7556	Intermediate Similarity	NPC226759
0.7556	Intermediate Similarity	NPC296044
0.7554	Intermediate Similarity	NPC472452
0.7554	Intermediate Similarity	NPC474475
0.7554	Intermediate Similarity	NPC474953
0.7554	Intermediate Similarity	NPC200726
0.7553	Intermediate Similarity	NPC305847
0.755	Intermediate Similarity	NPC94687
0.755	Intermediate Similarity	NPC476495
0.755	Intermediate Similarity	NPC106840
0.7549	Intermediate Similarity	NPC38964
0.7543	Intermediate Similarity	NPC472969
0.7542	Intermediate Similarity	NPC180901
0.7542	Intermediate Similarity	NPC300757
0.7541	Intermediate Similarity	NPC223006
0.7541	Intermediate Similarity	NPC134047
0.7541	Intermediate Similarity	NPC173729
0.7541	Intermediate Similarity	NPC272750
0.7541	Intermediate Similarity	NPC45943
0.754	Intermediate Similarity	NPC309692
0.7538	Intermediate Similarity	NPC314946
0.7528	Intermediate Similarity	NPC180388
0.7527	Intermediate Similarity	NPC187678
0.7527	Intermediate Similarity	NPC308267
0.7526	Intermediate Similarity	NPC477258
0.7525	Intermediate Similarity	NPC207971
0.7514	Intermediate Similarity	NPC31132
0.7514	Intermediate Similarity	NPC68619
0.7514	Intermediate Similarity	NPC473090
0.7514	Intermediate Similarity	NPC96501
0.7514	Intermediate Similarity	NPC177362
0.7513	Intermediate Similarity	NPC229234
0.7513	Intermediate Similarity	NPC302449
0.7512	Intermediate Similarity	NPC476496
0.7512	Intermediate Similarity	NPC19175
0.7512	Intermediate Similarity	NPC46990
0.75	Intermediate Similarity	NPC469438
0.75	Intermediate Similarity	NPC82533
0.75	Intermediate Similarity	NPC158148
0.75	Intermediate Similarity	NPC227062
0.75	Intermediate Similarity	NPC290759
0.75	Intermediate Similarity	NPC58766
0.75	Intermediate Similarity	NPC475686
0.75	Intermediate Similarity	NPC470324
0.75	Intermediate Similarity	NPC266176
0.75	Intermediate Similarity	NPC311339

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC162694 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	549
0.2-0.3	1228
0.3-0.4	2170
0.4-0.5	2460
0.5-0.6	1668
0.6-0.7	773
0.7-0.8	124
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8132	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.8115	Intermediate Similarity	NPD2491	Approved
0.8115	Intermediate Similarity	NPD3448	Approved
0.8115	Intermediate Similarity	NPD3057	Approved
0.8105	Intermediate Similarity	NPD4107	Approved
0.8081	Intermediate Similarity	NPD6385	Approved
0.8081	Intermediate Similarity	NPD6386	Approved
0.8065	Intermediate Similarity	NPD2490	Approved
0.8065	Intermediate Similarity	NPD2488	Approved
0.8021	Intermediate Similarity	NPD3533	Approved
0.8021	Intermediate Similarity	NPD2972	Approved
0.798	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7969	Intermediate Similarity	NPD4482	Phase 3
0.7969	Intermediate Similarity	NPD3450	Approved
0.7969	Intermediate Similarity	NPD2493	Approved
0.7969	Intermediate Similarity	NPD2494	Approved
0.7969	Intermediate Similarity	NPD3452	Approved
0.7938	Intermediate Similarity	NPD4582	Approved
0.7938	Intermediate Similarity	NPD4583	Approved
0.7906	Intermediate Similarity	NPD4420	Approved
0.7887	Intermediate Similarity	NPD4002	Approved
0.7887	Intermediate Similarity	NPD4004	Approved
0.7882	Intermediate Similarity	NPD7907	Approved
0.7871	Intermediate Similarity	NPD4111	Phase 1
0.7871	Intermediate Similarity	NPD4665	Approved
0.7835	Intermediate Similarity	NPD5005	Approved
0.7835	Intermediate Similarity	NPD5006	Approved
0.7796	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5676	Approved
0.776	Intermediate Similarity	NPD2975	Approved
0.776	Intermediate Similarity	NPD2974	Approved
0.776	Intermediate Similarity	NPD2973	Approved
0.7742	Intermediate Similarity	NPD2971	Approved
0.7742	Intermediate Similarity	NPD2968	Approved
0.774	Intermediate Similarity	NPD5353	Approved
0.7737	Intermediate Similarity	NPD7296	Approved
0.7732	Intermediate Similarity	NPD4580	Approved
0.7704	Intermediate Similarity	NPD7497	Discontinued
0.7692	Intermediate Similarity	NPD27	Approved
0.7692	Intermediate Similarity	NPD4481	Phase 3
0.7692	Intermediate Similarity	NPD2489	Approved
0.7663	Intermediate Similarity	NPD5313	Approved
0.7663	Intermediate Similarity	NPD5312	Approved
0.764	Intermediate Similarity	NPD5977	Approved
0.764	Intermediate Similarity	NPD5978	Approved
0.7637	Intermediate Similarity	NPD2970	Approved
0.7637	Intermediate Similarity	NPD2969	Approved
0.7637	Intermediate Similarity	NPD5242	Approved
0.7634	Intermediate Similarity	NPD7039	Approved
0.7634	Intermediate Similarity	NPD7038	Approved
0.7576	Intermediate Similarity	NPD4040	Phase 1
0.7557	Intermediate Similarity	NPD824	Approved
0.7553	Intermediate Similarity	NPD7313	Approved
0.7553	Intermediate Similarity	NPD7312	Approved
0.7553	Intermediate Similarity	NPD7311	Approved
0.7553	Intermediate Similarity	NPD7310	Approved
0.7526	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7309	Approved
0.7512	Intermediate Similarity	NPD5980	Discovery
0.75	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6997	Phase 2
0.75	Intermediate Similarity	NPD2898	Approved
0.7488	Intermediate Similarity	NPD7048	Phase 3
0.7486	Intermediate Similarity	NPD3051	Approved
0.7463	Intermediate Similarity	NPD7047	Phase 3
0.7462	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD3455	Phase 2
0.7443	Intermediate Similarity	NPD3641	Approved
0.7443	Intermediate Similarity	NPD3639	Approved
0.7443	Intermediate Similarity	NPD3640	Phase 3
0.7432	Intermediate Similarity	NPD6107	Approved
0.7411	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD3808	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7906	Approved
0.7391	Intermediate Similarity	NPD5710	Approved
0.7391	Intermediate Similarity	NPD5711	Approved
0.7374	Intermediate Similarity	NPD6873	Phase 2
0.7368	Intermediate Similarity	NPD4577	Approved
0.7368	Intermediate Similarity	NPD4578	Approved
0.7358	Intermediate Similarity	NPD6377	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD4663	Approved
0.7326	Intermediate Similarity	NPD7177	Discontinued
0.7317	Intermediate Similarity	NPD7827	Phase 1
0.7308	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5772	Approved
0.7293	Intermediate Similarity	NPD5773	Approved
0.7278	Intermediate Similarity	NPD4773	Phase 2
0.7278	Intermediate Similarity	NPD4772	Phase 2
0.7247	Intermediate Similarity	NPD1670	Discontinued
0.7241	Intermediate Similarity	NPD4237	Approved
0.7241	Intermediate Similarity	NPD4236	Phase 3
0.7236	Intermediate Similarity	NPD7565	Approved
0.7228	Intermediate Similarity	NPD6234	Discontinued
0.7222	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4210	Discontinued
0.7202	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD2978	Approved
0.7198	Intermediate Similarity	NPD2977	Approved
0.7188	Intermediate Similarity	NPD7281	Phase 3
0.7188	Intermediate Similarity	NPD7280	Phase 3
0.7182	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7110	Phase 1
0.7177	Intermediate Similarity	NPD8404	Phase 2
0.7159	Intermediate Similarity	NPD5241	Discontinued
0.7158	Intermediate Similarity	NPD2560	Approved
0.7158	Intermediate Similarity	NPD2563	Approved
0.715	Intermediate Similarity	NPD6853	Approved
0.715	Intermediate Similarity	NPD6851	Approved
0.7136	Intermediate Similarity	NPD5564	Approved
0.7135	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7291	Discontinued
0.7127	Intermediate Similarity	NPD6876	Approved
0.7127	Intermediate Similarity	NPD6875	Approved
0.712	Intermediate Similarity	NPD6297	Approved
0.712	Intermediate Similarity	NPD3823	Discontinued
0.7112	Intermediate Similarity	NPD7315	Approved
0.7112	Intermediate Similarity	NPD6071	Discontinued
0.7111	Intermediate Similarity	NPD3687	Approved
0.7111	Intermediate Similarity	NPD3686	Approved
0.711	Intermediate Similarity	NPD6625	Approved
0.7108	Intermediate Similarity	NPD7999	Approved
0.7105	Intermediate Similarity	NPD5844	Phase 1
0.7104	Intermediate Similarity	NPD1465	Phase 2
0.7086	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7685	Pre-registration
0.7081	Intermediate Similarity	NPD7930	Approved
0.7079	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD3863	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7228	Approved
0.7053	Intermediate Similarity	NPD2163	Approved
0.7052	Intermediate Similarity	NPD2569	Approved
0.7052	Intermediate Similarity	NPD2567	Approved
0.7049	Intermediate Similarity	NPD37	Approved
0.7049	Intermediate Similarity	NPD1934	Approved
0.7044	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7701	Phase 2
0.7037	Intermediate Similarity	NPD3451	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD3473	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD230	Phase 1
0.7027	Intermediate Similarity	NPD4967	Phase 2
0.7027	Intermediate Similarity	NPD4966	Approved
0.7027	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD4965	Approved
0.7022	Intermediate Similarity	NPD6666	Approved
0.7022	Intermediate Similarity	NPD6667	Approved
0.7021	Intermediate Similarity	NPD6232	Discontinued
0.7011	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4628	Phase 3
0.7005	Intermediate Similarity	NPD7235	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7473	Discontinued
0.7	Intermediate Similarity	NPD4361	Phase 2
0.7	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD8319	Approved
0.6976	Remote Similarity	NPD8320	Phase 1
0.6974	Remote Similarity	NPD8053	Approved
0.6974	Remote Similarity	NPD8054	Approved
0.6963	Remote Similarity	NPD3818	Discontinued
0.6963	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7427	Discontinued
0.6959	Remote Similarity	NPD7549	Discontinued
0.6957	Remote Similarity	NPD7577	Discontinued
0.695	Remote Similarity	NPD4413	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD4584	Approved
0.6944	Remote Similarity	NPD2533	Approved
0.6944	Remote Similarity	NPD3146	Approved
0.6944	Remote Similarity	NPD2534	Approved
0.6944	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2532	Approved
0.6942	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD3882	Suspended
0.6931	Remote Similarity	NPD4010	Discontinued
0.6931	Remote Similarity	NPD4166	Phase 2
0.6927	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6836	Approved
0.6915	Remote Similarity	NPD5494	Approved
0.6915	Remote Similarity	NPD4666	Phase 3
0.6906	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD5038	Approved
0.6904	Remote Similarity	NPD5037	Approved
0.6898	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7833	Phase 2
0.6898	Remote Similarity	NPD7831	Phase 2
0.6898	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8285	Discontinued
0.6897	Remote Similarity	NPD7811	Phase 3
0.6897	Remote Similarity	NPD7810	Phase 3
0.6891	Remote Similarity	NPD5441	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD6618	Phase 2
0.6885	Remote Similarity	NPD2649	Approved
0.6885	Remote Similarity	NPD2651	Approved
0.6882	Remote Similarity	NPD9494	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data