NPASS Compound

Structure

CID4304 OpenBabel06191715322D 23 26 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 -4.5000 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 0.0000 -3.0000 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 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 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 3 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 3 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 -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 -2.5981 -3.5000 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 19 1 0 0 0 0 2 21 1 0 0 0 0 3 22 1 0 0 0 0 4 5 1 0 0 0 0 4 10 2 0 0 0 0 6 7 1 0 0 0 0 6 10 1 0 0 0 0 7 19 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 11 12 1 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 13 5 1 6 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 15 2 0 0 0 0 14 21 1 0 0 0 0 15 22 1 0 0 0 0 16 17 1 0 0 0 0 17 10 1 1 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	317.16
Volume:	321.27
LogP:	1.695
LogD:	2.081
LogS:	-1.826
# Rotatable Bonds:	2
TPSA:	51.16
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.848
Synthetic Accessibility Score:	4.141
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.648
MDCK Permeability:	1.0431019290990662e-05
Pgp-inhibitor:	0.022
Pgp-substrate:	0.833
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.97
Plasma Protein Binding (PPB):	63.89386749267578%
Volume Distribution (VD):	2.762
Pgp-substrate:	30.359169006347656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.776
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.942
CYP2C9-inhibitor:	0.016
CYP2C9-substrate:	0.53
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.894

ADMET: Excretion

Clearance (CL):	8.197
Half-life (T1/2):	0.751

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.199
Drug-inuced Liver Injury (DILI):	0.067
AMES Toxicity:	0.437
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.063
Carcinogencity:	0.88
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC4304

Natural Product ID:	NPC4304
*Common Name:**	(5Ar,11Cs)-9,10-Dimethoxy-1-Methyl-3,5,5A,7,11B,11C-Hexahydro-2H-Isochromeno[3,4-G]Indol-7-Ol
IUPAC Name:	(5aR,11cS)-9,10-dimethoxy-1-methyl-3,5,5a,7,11b,11c-hexahydro-2H-isochromeno[3,4-g]indol-7-ol
Synonyms:
Standard InCHIKey:	VHYYSQODIQWPDO-OEWOMKROSA-N
Standard InCHI:	InChI=1S/C18H23NO4/c1-19-7-6-10-4-5-13-16(17(10)19)11-8-14(21-2)15(22-3)9-12(11)18(20)23-13/h4,8-9,13,16-18,20H,5-7H2,1-3H3/t13-,16?,17-,18?/m1/s1
SMILES:	COc1cc2C3[C@@H](CC=C4[C@H]3N(C)CC4)OC(c2cc1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1885951
PubChem CID:	44202119
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
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18356045]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	Turkey	n.a.	PMID[19299148]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	stem	n.a.	PMID[20066175]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21510636]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25061748]
NPO9942.1	Narcissus tazetta var. chinensis	Varieties	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9074	Narcissus papyraceus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22747	Lycoris sanguinea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22747	Lycoris sanguinea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9942.1	Narcissus tazetta var. chinensis	Varieties	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9074	Narcissus papyraceus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22747	Lycoris sanguinea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5400	Lycoris aurea	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9074	Narcissus papyraceus	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9927	Crinum asiaticum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27843	Lycoris radiata	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25694	Leucojum aestivum	Species	Amaryllidaceae	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
Potency	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	100000.0	nM	PMID[491666]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	1636.0	nM	PMID[491666]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	70794.6	nM	PMID[491666]

☑ 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 NPC4304 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	242
0.1-0.2	1197
0.2-0.3	3653
0.3-0.4	11331
0.4-0.5	7966
0.5-0.6	12165
0.6-0.7	4747
0.7-0.8	1236
0.8-0.85	89
0.85-0.9	46
0.9-0.95	23
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9177	High Similarity	NPC181653
0.9177	High Similarity	NPC190332
0.9177	High Similarity	NPC252960
0.9172	High Similarity	NPC180306
0.9108	High Similarity	NPC320104
0.9074	High Similarity	NPC237044
0.9057	High Similarity	NPC100566
0.9018	High Similarity	NPC474325
0.9012	High Similarity	NPC304675
0.8987	High Similarity	NPC218614
0.8981	High Similarity	NPC249274
0.8981	High Similarity	NPC205167
0.8963	High Similarity	NPC474745
0.8889	High Similarity	NPC470739
0.8889	High Similarity	NPC225597
0.8889	High Similarity	NPC477640
0.8875	High Similarity	NPC476002
0.8827	High Similarity	NPC474475
0.882	High Similarity	NPC57812
0.882	High Similarity	NPC474324
0.8802	High Similarity	NPC475981
0.8802	High Similarity	NPC474746
0.8765	High Similarity	NPC266176
0.8765	High Similarity	NPC82533
0.8765	High Similarity	NPC475686
0.8765	High Similarity	NPC475845
0.8765	High Similarity	NPC58766
0.8765	High Similarity	NPC290759
0.8765	High Similarity	NPC158148
0.8712	High Similarity	NPC474708
0.8698	High Similarity	NPC230098
0.8667	High Similarity	NPC187678
0.8625	High Similarity	NPC97072
0.8625	High Similarity	NPC215829
0.8614	High Similarity	NPC474470
0.8606	High Similarity	NPC2314
0.8598	High Similarity	NPC311991
0.8563	High Similarity	NPC294790
0.8563	High Similarity	NPC148693
0.8563	High Similarity	NPC118633
0.8562	High Similarity	NPC59028
0.8562	High Similarity	NPC92191
0.8554	High Similarity	NPC49353
0.8506	High Similarity	NPC33256
0.8452	Intermediate Similarity	NPC15919
0.8438	Intermediate Similarity	NPC147091
0.8421	Intermediate Similarity	NPC9867
0.8412	Intermediate Similarity	NPC248642
0.8402	Intermediate Similarity	NPC244554
0.8402	Intermediate Similarity	NPC99179
0.8375	Intermediate Similarity	NPC78733
0.8372	Intermediate Similarity	NPC162694
0.8364	Intermediate Similarity	NPC301189
0.8364	Intermediate Similarity	NPC298186
0.8363	Intermediate Similarity	NPC156576
0.8354	Intermediate Similarity	NPC274026
0.8333	Intermediate Similarity	NPC69360
0.8323	Intermediate Similarity	NPC65403
0.8323	Intermediate Similarity	NPC57272
0.8303	Intermediate Similarity	NPC124657
0.8294	Intermediate Similarity	NPC126284
0.8284	Intermediate Similarity	NPC35680
0.8282	Intermediate Similarity	NPC165797
0.8263	Intermediate Similarity	NPC75958
0.8263	Intermediate Similarity	NPC474953
0.8253	Intermediate Similarity	NPC150879
0.825	Intermediate Similarity	NPC148898
0.8242	Intermediate Similarity	NPC247972
0.8235	Intermediate Similarity	NPC114364
0.8235	Intermediate Similarity	NPC320223
0.8228	Intermediate Similarity	NPC475959
0.8225	Intermediate Similarity	NPC199465
0.8225	Intermediate Similarity	NPC128560
0.8225	Intermediate Similarity	NPC229166
0.8221	Intermediate Similarity	NPC111485
0.821	Intermediate Similarity	NPC323443
0.821	Intermediate Similarity	NPC180756
0.8198	Intermediate Similarity	NPC275132
0.8144	Intermediate Similarity	NPC247389
0.8137	Intermediate Similarity	NPC82285
0.8137	Intermediate Similarity	NPC133011
0.8133	Intermediate Similarity	NPC16805
0.8133	Intermediate Similarity	NPC302527
0.8133	Intermediate Similarity	NPC238530
0.8133	Intermediate Similarity	NPC232514
0.8133	Intermediate Similarity	NPC276944
0.8133	Intermediate Similarity	NPC167546
0.8098	Intermediate Similarity	NPC146288
0.8092	Intermediate Similarity	NPC233718
0.8087	Intermediate Similarity	NPC80472
0.8084	Intermediate Similarity	NPC219341
0.8084	Intermediate Similarity	NPC476432
0.8084	Intermediate Similarity	NPC24264
0.8072	Intermediate Similarity	NPC233650
0.8057	Intermediate Similarity	NPC214116
0.8049	Intermediate Similarity	NPC78359
0.8049	Intermediate Similarity	NPC315707
0.8049	Intermediate Similarity	NPC65490
0.8049	Intermediate Similarity	NPC40389
0.8049	Intermediate Similarity	NPC148014
0.8038	Intermediate Similarity	NPC130926
0.8038	Intermediate Similarity	NPC185838
0.8037	Intermediate Similarity	NPC41178
0.8037	Intermediate Similarity	NPC138487
0.8037	Intermediate Similarity	NPC216459
0.8036	Intermediate Similarity	NPC210918
0.8036	Intermediate Similarity	NPC298979
0.8035	Intermediate Similarity	NPC305847
0.8025	Intermediate Similarity	NPC270811
0.8025	Intermediate Similarity	NPC233029
0.8025	Intermediate Similarity	NPC223124
0.8025	Intermediate Similarity	NPC210148
0.8025	Intermediate Similarity	NPC471073
0.8024	Intermediate Similarity	NPC54125
0.8024	Intermediate Similarity	NPC89199
0.8024	Intermediate Similarity	NPC225774
0.8024	Intermediate Similarity	NPC134858
0.8	Intermediate Similarity	NPC428
0.8	Intermediate Similarity	NPC246587
0.8	Intermediate Similarity	NPC24233
0.8	Intermediate Similarity	NPC135538
0.8	Intermediate Similarity	NPC477080
0.8	Intermediate Similarity	NPC147390
0.8	Intermediate Similarity	NPC476571
0.7989	Intermediate Similarity	NPC116284
0.7989	Intermediate Similarity	NPC302449
0.7988	Intermediate Similarity	NPC182257
0.7988	Intermediate Similarity	NPC160570
0.7978	Intermediate Similarity	NPC94499
0.7965	Intermediate Similarity	NPC241704
0.795	Intermediate Similarity	NPC211296
0.7943	Intermediate Similarity	NPC135772
0.7937	Intermediate Similarity	NPC476151
0.7937	Intermediate Similarity	NPC179825
0.7937	Intermediate Similarity	NPC191376
0.7937	Intermediate Similarity	NPC321505
0.7935	Intermediate Similarity	NPC193528
0.7931	Intermediate Similarity	NPC477561
0.7931	Intermediate Similarity	NPC476574
0.7931	Intermediate Similarity	NPC155442
0.7931	Intermediate Similarity	NPC474607
0.7931	Intermediate Similarity	NPC312918
0.7929	Intermediate Similarity	NPC474931
0.7929	Intermediate Similarity	NPC81218
0.7929	Intermediate Similarity	NPC306555
0.7929	Intermediate Similarity	NPC117188
0.7929	Intermediate Similarity	NPC205421
0.7929	Intermediate Similarity	NPC304846
0.7929	Intermediate Similarity	NPC210140
0.7929	Intermediate Similarity	NPC12053
0.7929	Intermediate Similarity	NPC145832
0.7929	Intermediate Similarity	NPC158376
0.7922	Intermediate Similarity	NPC11147
0.7921	Intermediate Similarity	NPC475754
0.7917	Intermediate Similarity	NPC212794
0.7917	Intermediate Similarity	NPC306843
0.7917	Intermediate Similarity	NPC96603
0.7917	Intermediate Similarity	NPC13504
0.7917	Intermediate Similarity	NPC231198
0.7917	Intermediate Similarity	NPC196447
0.7917	Intermediate Similarity	NPC253043
0.7917	Intermediate Similarity	NPC78222
0.7917	Intermediate Similarity	NPC136508
0.7917	Intermediate Similarity	NPC477563
0.7907	Intermediate Similarity	NPC329969
0.7901	Intermediate Similarity	NPC88249
0.7901	Intermediate Similarity	NPC97221
0.7901	Intermediate Similarity	NPC220858
0.7901	Intermediate Similarity	NPC192768
0.7901	Intermediate Similarity	NPC151895
0.7901	Intermediate Similarity	NPC223125
0.7898	Intermediate Similarity	NPC474915
0.7898	Intermediate Similarity	NPC213206
0.7898	Intermediate Similarity	NPC328750
0.7898	Intermediate Similarity	NPC188163
0.7895	Intermediate Similarity	NPC149090
0.7895	Intermediate Similarity	NPC19520
0.7886	Intermediate Similarity	NPC476575
0.7886	Intermediate Similarity	NPC474650
0.7879	Intermediate Similarity	NPC234392
0.7879	Intermediate Similarity	NPC160931
0.7879	Intermediate Similarity	NPC37205
0.7879	Intermediate Similarity	NPC186063
0.7879	Intermediate Similarity	NPC31311
0.7874	Intermediate Similarity	NPC32154
0.7874	Intermediate Similarity	NPC475794
0.7871	Intermediate Similarity	NPC7018
0.7861	Intermediate Similarity	NPC283999
0.7857	Intermediate Similarity	NPC324144
0.7857	Intermediate Similarity	NPC59567
0.7853	Intermediate Similarity	NPC57036
0.7844	Intermediate Similarity	NPC266753
0.7844	Intermediate Similarity	NPC306902
0.7844	Intermediate Similarity	NPC232924
0.7844	Intermediate Similarity	NPC477559
0.7844	Intermediate Similarity	NPC160298
0.7844	Intermediate Similarity	NPC18402
0.784	Intermediate Similarity	NPC477565
0.784	Intermediate Similarity	NPC103379
0.7836	Intermediate Similarity	NPC6152

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 NPC4304 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	609
0.2-0.3	1058
0.3-0.4	2429
0.4-0.5	2553
0.5-0.6	1504
0.6-0.7	682
0.7-0.8	144
0.8-0.85	13
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8476	Intermediate Similarity	NPD2970	Approved
0.8476	Intermediate Similarity	NPD2969	Approved
0.8313	Intermediate Similarity	NPD27	Approved
0.8313	Intermediate Similarity	NPD2489	Approved
0.8303	Intermediate Similarity	NPD3051	Approved
0.821	Intermediate Similarity	NPD5772	Approved
0.821	Intermediate Similarity	NPD5773	Approved
0.8199	Intermediate Similarity	NPD4772	Phase 2
0.8199	Intermediate Similarity	NPD4773	Phase 2
0.8194	Intermediate Similarity	NPD4237	Approved
0.8194	Intermediate Similarity	NPD4236	Phase 3
0.8098	Intermediate Similarity	NPD2978	Approved
0.8098	Intermediate Similarity	NPD2977	Approved
0.8095	Intermediate Similarity	NPD4481	Phase 3
0.8089	Intermediate Similarity	NPD5241	Discontinued
0.8049	Intermediate Similarity	NPD2560	Approved
0.8049	Intermediate Similarity	NPD2563	Approved
0.8035	Intermediate Similarity	NPD7312	Approved
0.8035	Intermediate Similarity	NPD7313	Approved
0.8035	Intermediate Similarity	NPD7311	Approved
0.8035	Intermediate Similarity	NPD7310	Approved
0.7989	Intermediate Similarity	NPD7309	Approved
0.7976	Intermediate Similarity	NPD6071	Discontinued
0.7975	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4663	Approved
0.7879	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7906	Approved
0.7829	Intermediate Similarity	NPD4577	Approved
0.7829	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7829	Intermediate Similarity	NPD4578	Approved
0.7791	Intermediate Similarity	NPD4210	Discontinued
0.7722	Intermediate Similarity	NPD7296	Approved
0.7716	Intermediate Similarity	NPD4584	Approved
0.7702	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2238	Phase 2
0.7625	Intermediate Similarity	NPD3060	Approved
0.761	Intermediate Similarity	NPD1375	Discontinued
0.7607	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6107	Approved
0.7584	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7243	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD3705	Approved
0.753	Intermediate Similarity	NPD4005	Discontinued
0.7529	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7833	Phase 2
0.7529	Intermediate Similarity	NPD7831	Phase 2
0.7516	Intermediate Similarity	NPD5177	Phase 3
0.7515	Intermediate Similarity	NPD3641	Approved
0.7515	Intermediate Similarity	NPD3639	Approved
0.7515	Intermediate Similarity	NPD3640	Phase 3
0.75	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD2490	Approved
0.7473	Intermediate Similarity	NPD2488	Approved
0.7471	Intermediate Similarity	NPD2898	Approved
0.747	Intermediate Similarity	NPD3687	Approved
0.747	Intermediate Similarity	NPD3686	Approved
0.743	Intermediate Similarity	NPD2971	Approved
0.743	Intermediate Similarity	NPD2968	Approved
0.7427	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD5604	Discontinued
0.7419	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD2122	Discontinued
0.7407	Intermediate Similarity	NPD4162	Approved
0.7396	Intermediate Similarity	NPD7298	Approved
0.7389	Intermediate Similarity	NPD8053	Approved
0.7389	Intermediate Similarity	NPD8054	Approved
0.738	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD6666	Approved
0.7378	Intermediate Similarity	NPD6667	Approved
0.7375	Intermediate Similarity	NPD1753	Discontinued
0.7366	Intermediate Similarity	NPD2975	Approved
0.7366	Intermediate Similarity	NPD2974	Approved
0.7366	Intermediate Similarity	NPD2973	Approved
0.7362	Intermediate Similarity	NPD6331	Phase 2
0.7356	Intermediate Similarity	NPD4010	Discontinued
0.7349	Intermediate Similarity	NPD7526	Approved
0.7349	Intermediate Similarity	NPD52	Approved
0.7349	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD5313	Approved
0.7345	Intermediate Similarity	NPD8156	Discontinued
0.7345	Intermediate Similarity	NPD5312	Approved
0.734	Intermediate Similarity	NPD4580	Approved
0.7333	Intermediate Similarity	NPD7281	Phase 3
0.7333	Intermediate Similarity	NPD7280	Phase 3
0.7326	Intermediate Similarity	NPD4420	Approved
0.7325	Intermediate Similarity	NPD5718	Phase 2
0.7321	Intermediate Similarity	NPD4017	Approved
0.7317	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2677	Approved
0.7312	Intermediate Similarity	NPD6895	Approved
0.7312	Intermediate Similarity	NPD6896	Approved
0.7312	Intermediate Similarity	NPD5582	Discontinued
0.7305	Intermediate Similarity	NPD4727	Phase 1
0.7305	Intermediate Similarity	NPD6030	Approved
0.7305	Intermediate Similarity	NPD6031	Approved
0.7302	Intermediate Similarity	NPD3450	Approved
0.7302	Intermediate Similarity	NPD2494	Approved
0.7302	Intermediate Similarity	NPD2493	Approved
0.7302	Intermediate Similarity	NPD3452	Approved
0.7301	Intermediate Similarity	NPD6674	Discontinued
0.7294	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD4123	Phase 3
0.7288	Intermediate Similarity	NPD8099	Discontinued
0.7288	Intermediate Similarity	NPD8251	Approved
0.7288	Intermediate Similarity	NPD8252	Approved
0.7277	Intermediate Similarity	NPD4583	Approved
0.7277	Intermediate Similarity	NPD4582	Approved
0.7273	Intermediate Similarity	NPD7124	Phase 2
0.7268	Intermediate Similarity	NPD6841	Approved
0.7268	Intermediate Similarity	NPD6842	Approved
0.7268	Intermediate Similarity	NPD6843	Phase 3
0.7267	Intermediate Similarity	NPD4108	Discontinued
0.7263	Intermediate Similarity	NPD5006	Approved
0.7263	Intermediate Similarity	NPD3057	Approved
0.7263	Intermediate Similarity	NPD5005	Approved
0.7257	Intermediate Similarity	NPD4166	Phase 2
0.7256	Intermediate Similarity	NPD5754	Discontinued
0.7255	Intermediate Similarity	NPD2233	Approved
0.7255	Intermediate Similarity	NPD2230	Approved
0.7255	Intermediate Similarity	NPD2232	Approved
0.7241	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7037	Approved
0.7238	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD3110	Approved
0.7233	Intermediate Similarity	NPD3109	Approved
0.7225	Intermediate Similarity	NPD4002	Approved
0.7225	Intermediate Similarity	NPD4004	Approved
0.7222	Intermediate Similarity	NPD2161	Phase 2
0.7212	Intermediate Similarity	NPD3692	Discontinued
0.7193	Intermediate Similarity	NPD3382	Approved
0.7193	Intermediate Similarity	NPD37	Approved
0.7193	Intermediate Similarity	NPD3384	Approved
0.7193	Intermediate Similarity	NPD3383	Approved
0.7184	Intermediate Similarity	NPD5709	Phase 3
0.7178	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD2972	Approved
0.7173	Intermediate Similarity	NPD3533	Approved
0.7171	Intermediate Similarity	NPD2667	Approved
0.7171	Intermediate Similarity	NPD2668	Approved
0.7168	Intermediate Similarity	NPD4967	Phase 2
0.7168	Intermediate Similarity	NPD4965	Approved
0.7168	Intermediate Similarity	NPD4966	Approved
0.7152	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD42	Phase 2
0.7151	Intermediate Similarity	NPD6042	Phase 2
0.7143	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4666	Phase 3
0.7143	Intermediate Similarity	NPD823	Approved
0.7143	Intermediate Similarity	NPD2492	Phase 1
0.7143	Intermediate Similarity	NPD817	Approved
0.7128	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD1774	Approved
0.7107	Intermediate Similarity	NPD7827	Phase 1
0.7099	Intermediate Similarity	NPD6111	Discontinued
0.7094	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3448	Approved
0.7083	Intermediate Similarity	NPD2491	Approved
0.7076	Intermediate Similarity	NPD4675	Approved
0.7076	Intermediate Similarity	NPD4678	Approved
0.7072	Intermediate Similarity	NPD7007	Discovery
0.7069	Intermediate Similarity	NPD6788	Approved
0.7068	Intermediate Similarity	NPD4107	Approved
0.7066	Intermediate Similarity	NPD3122	Phase 3
0.7063	Intermediate Similarity	NPD1136	Approved
0.7063	Intermediate Similarity	NPD1130	Approved
0.7063	Intermediate Similarity	NPD1132	Approved
0.7041	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6090	Discontinued
0.7039	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6386	Approved
0.7035	Intermediate Similarity	NPD6385	Approved
0.7033	Intermediate Similarity	NPD7038	Approved
0.7033	Intermediate Similarity	NPD7039	Approved
0.703	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3636	Approved
0.7025	Intermediate Similarity	NPD3637	Approved
0.7025	Intermediate Similarity	NPD3635	Approved
0.7024	Intermediate Similarity	NPD2420	Approved
0.7024	Intermediate Similarity	NPD2421	Approved
0.7024	Intermediate Similarity	NPD3124	Discontinued
0.7019	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3620	Phase 2
0.7018	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6853	Approved
0.7011	Intermediate Similarity	NPD6851	Approved
0.701	Intermediate Similarity	NPD4040	Phase 1
0.7006	Intermediate Similarity	NPD4098	Discontinued
0.7006	Intermediate Similarity	NPD4103	Phase 2
0.7006	Intermediate Similarity	NPD4104	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5525	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD598	Approved
0.7	Intermediate Similarity	NPD7047	Phase 3
0.7	Intermediate Similarity	NPD597	Approved
0.7	Intermediate Similarity	NPD7228	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