NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	264.14
Volume:	269.578
LogP:	2.944
LogD:	2.846
LogS:	-3.152
# Rotatable Bonds:	0
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.496
Synthetic Accessibility Score:	4.607
Fsp3:	0.733
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.74
MDCK Permeability:	4.9389975174563006e-05
Pgp-inhibitor:	0.208
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.135
30% Bioavailability (F30%):	0.885

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.157
Plasma Protein Binding (PPB):	68.63398742675781%
Volume Distribution (VD):	0.571
Pgp-substrate:	41.2274284362793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.197
CYP1A2-substrate:	0.175
CYP2C19-inhibitor:	0.245
CYP2C19-substrate:	0.749
CYP2C9-inhibitor:	0.13
CYP2C9-substrate:	0.063
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.676
CYP3A4-substrate:	0.357

ADMET: Excretion

Clearance (CL):	15.67
Half-life (T1/2):	0.573

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.26
Drug-inuced Liver Injury (DILI):	0.862
AMES Toxicity:	0.084
Rat Oral Acute Toxicity:	0.321
Maximum Recommended Daily Dose:	0.787
Skin Sensitization:	0.927
Carcinogencity:	0.728
Eye Corrosion:	0.908
Eye Irritation:	0.903
Respiratory Toxicity:	0.825

Download Data

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

Natural Product: NPC47635

Natural Product ID:	NPC47635
*Common Name:**	(4As,5R,6As,10As)-5,10A-Dimethyl-9-Methylidene-1,4,4A,5,6,6A,9A,10-Octahydrofuro[3,4]Cyclohepta[5,7-B]Pyran-3,8-Dione
IUPAC Name:	(4aS,5R,6aS,10aS)-5,10a-dimethyl-9-methylidene-1,4,4a,5,6,6a,9a,10-octahydrofuro[3,4]cyclohepta[5,7-b]pyran-3,8-dione
Synonyms:
Standard InCHIKey:	GKYRUDQNQRLJRF-XGOSFXCESA-N
Standard InCHI:	InChI=1S/C15H20O4/c1-8-4-12-10(9(2)14(17)19-12)6-15(3)7-18-13(16)5-11(8)15/h8,10-12H,2,4-7H2,1,3H3/t8-,10?,11+,12+,15-/m1/s1
SMILES:	C[C@@H]1C[C@H]2C(C[C@]3(C)COC(=O)C[C@@H]13)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1975417
PubChem CID:	10400578
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO21046	Verbena triphylla	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1885	Asteraceae spp.	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21046	Verbena triphylla	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21046	Verbena triphylla	Species	Verbenaceae	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.	21627.19	nM	PMID[536878]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	23280.91	nM	PMID[536878]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	21727.01	nM	PMID[536878]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	49090.79	nM	PMID[536878]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	16106.46	nM	PMID[536878]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	21928.05	nM	PMID[536878]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	34276.78	nM	PMID[536878]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	17947.34	nM	PMID[536878]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	17538.81	nM	PMID[536878]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	27989.81	nM	PMID[536878]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	27478.94	nM	PMID[536878]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	44771.33	nM	PMID[536878]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	97274.72	nM	PMID[536878]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	17947.34	nM	PMID[536878]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	53088.44	nM	PMID[536878]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	28575.91	nM	PMID[536878]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	22803.42	nM	PMID[536878]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	20230.19	nM	PMID[536878]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	16710.91	nM	PMID[536878]
NPT573	Cell Line	M19-MEL	Homo sapiens	GI50	n.a.	34514.37	nM	PMID[536878]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	3556.31	nM	PMID[536878]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	20464.45	nM	PMID[536878]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	14927.94	nM	PMID[536878]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	14421.15	nM	PMID[536878]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	21478.3	nM	PMID[536878]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	21379.62	nM	PMID[536878]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	22803.42	nM	PMID[536878]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	24888.57	nM	PMID[536878]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	35809.64	nM	PMID[536878]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	27797.13	nM	PMID[536878]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	18450.15	nM	PMID[536878]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	30060.76	nM	PMID[536878]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	32136.61	nM	PMID[536878]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	29376.5	nM	PMID[536878]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	21037.78	nM	PMID[536878]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	27415.74	nM	PMID[536878]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	27542.29	nM	PMID[536878]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	97723.72	nM	PMID[536878]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	19906.73	nM	PMID[536878]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	25941.79	nM	PMID[536878]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	18793.17	nM	PMID[536878]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	19230.92	nM	PMID[536878]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	17988.71	nM	PMID[536878]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	51641.64	nM	PMID[536878]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	21627.19	nM	PMID[536878]
NPT577	Cell Line	RXF 631	Homo sapiens	GI50	n.a.	17179.08	nM	PMID[536878]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	21183.61	nM	PMID[536878]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	28575.91	nM	PMID[536878]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	12882.5	nM	PMID[536878]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	23388.37	nM	PMID[536878]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	19678.86	nM	PMID[536878]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	17538.81	nM	PMID[536878]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	20941.12	nM	PMID[536878]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	36475.39	nM	PMID[536878]

☑ 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 NPC47635 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	184
0.1-0.2	1565
0.2-0.3	6311
0.3-0.4	14652
0.4-0.5	8800
0.5-0.6	7268
0.6-0.7	3401
0.7-0.8	495
0.8-0.85	19
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8701	High Similarity	NPC471491
0.8642	High Similarity	NPC246076
0.8625	High Similarity	NPC293418
0.8625	High Similarity	NPC73052
0.8625	High Similarity	NPC290508
0.8571	High Similarity	NPC24728
0.8537	High Similarity	NPC54468
0.8471	Intermediate Similarity	NPC471149
0.8452	Intermediate Similarity	NPC470242
0.8452	Intermediate Similarity	NPC56593
0.8395	Intermediate Similarity	NPC6823
0.8391	Intermediate Similarity	NPC286341
0.8391	Intermediate Similarity	NPC191339
0.8372	Intermediate Similarity	NPC155935
0.8372	Intermediate Similarity	NPC283409
0.8353	Intermediate Similarity	NPC118601
0.8353	Intermediate Similarity	NPC175293
0.8333	Intermediate Similarity	NPC320537
0.8333	Intermediate Similarity	NPC143979
0.8295	Intermediate Similarity	NPC473234
0.8295	Intermediate Similarity	NPC200237
0.8295	Intermediate Similarity	NPC60386
0.8295	Intermediate Similarity	NPC153590
0.8295	Intermediate Similarity	NPC473263
0.8295	Intermediate Similarity	NPC308656
0.8295	Intermediate Similarity	NPC473273
0.8276	Intermediate Similarity	NPC35809
0.8276	Intermediate Similarity	NPC54065
0.8276	Intermediate Similarity	NPC297474
0.8256	Intermediate Similarity	NPC178875
0.825	Intermediate Similarity	NPC208223
0.8235	Intermediate Similarity	NPC64153
0.8235	Intermediate Similarity	NPC238593
0.8235	Intermediate Similarity	NPC304558
0.8202	Intermediate Similarity	NPC473434
0.8202	Intermediate Similarity	NPC471446
0.8202	Intermediate Similarity	NPC473331
0.8202	Intermediate Similarity	NPC474841
0.8182	Intermediate Similarity	NPC133888
0.8182	Intermediate Similarity	NPC57304
0.8182	Intermediate Similarity	NPC293001
0.8182	Intermediate Similarity	NPC29821
0.8182	Intermediate Similarity	NPC171360
0.8182	Intermediate Similarity	NPC63193
0.8182	Intermediate Similarity	NPC35959
0.8171	Intermediate Similarity	NPC474981
0.814	Intermediate Similarity	NPC270270
0.814	Intermediate Similarity	NPC190753
0.8118	Intermediate Similarity	NPC284534
0.8118	Intermediate Similarity	NPC161957
0.8118	Intermediate Similarity	NPC204105
0.8118	Intermediate Similarity	NPC235792
0.8118	Intermediate Similarity	NPC300082
0.8072	Intermediate Similarity	NPC38642
0.8068	Intermediate Similarity	NPC62815
0.8068	Intermediate Similarity	NPC475776
0.8046	Intermediate Similarity	NPC207114
0.8046	Intermediate Similarity	NPC217983
0.8046	Intermediate Similarity	NPC79549
0.8025	Intermediate Similarity	NPC470240
0.8025	Intermediate Similarity	NPC476794
0.8023	Intermediate Similarity	NPC187661
0.8022	Intermediate Similarity	NPC91771
0.8022	Intermediate Similarity	NPC142529
0.8	Intermediate Similarity	NPC470011
0.8	Intermediate Similarity	NPC470238
0.8	Intermediate Similarity	NPC194859
0.8	Intermediate Similarity	NPC224386
0.8	Intermediate Similarity	NPC138647
0.7976	Intermediate Similarity	NPC226988
0.7955	Intermediate Similarity	NPC472872
0.7955	Intermediate Similarity	NPC12872
0.7955	Intermediate Similarity	NPC116620
0.7955	Intermediate Similarity	NPC215556
0.7955	Intermediate Similarity	NPC168679
0.7952	Intermediate Similarity	NPC69271
0.7952	Intermediate Similarity	NPC276356
0.7952	Intermediate Similarity	NPC74673
0.7935	Intermediate Similarity	NPC213947
0.7935	Intermediate Similarity	NPC170143
0.7935	Intermediate Similarity	NPC108475
0.7931	Intermediate Similarity	NPC201658
0.7912	Intermediate Similarity	NPC167893
0.7907	Intermediate Similarity	NPC33570
0.7907	Intermediate Similarity	NPC21471
0.7889	Intermediate Similarity	NPC135776
0.7889	Intermediate Similarity	NPC475657
0.7882	Intermediate Similarity	NPC215294
0.7882	Intermediate Similarity	NPC194637
0.7882	Intermediate Similarity	NPC128429
0.7882	Intermediate Similarity	NPC272814
0.7882	Intermediate Similarity	NPC39588
0.7882	Intermediate Similarity	NPC257358
0.7882	Intermediate Similarity	NPC474472
0.7882	Intermediate Similarity	NPC318468
0.7865	Intermediate Similarity	NPC216284
0.7865	Intermediate Similarity	NPC19087
0.7841	Intermediate Similarity	NPC91248
0.7831	Intermediate Similarity	NPC182550
0.7826	Intermediate Similarity	NPC18019
0.7826	Intermediate Similarity	NPC228766
0.7826	Intermediate Similarity	NPC24956
0.7826	Intermediate Similarity	NPC165528
0.7821	Intermediate Similarity	NPC5714
0.7816	Intermediate Similarity	NPC284902
0.7816	Intermediate Similarity	NPC236692
0.7816	Intermediate Similarity	NPC67493
0.7816	Intermediate Similarity	NPC309757
0.7805	Intermediate Similarity	NPC65603
0.7802	Intermediate Similarity	NPC148000
0.7802	Intermediate Similarity	NPC469596
0.7802	Intermediate Similarity	NPC225474
0.7791	Intermediate Similarity	NPC219011
0.7778	Intermediate Similarity	NPC226669
0.7778	Intermediate Similarity	NPC74103
0.7778	Intermediate Similarity	NPC131209
0.7778	Intermediate Similarity	NPC138408
0.7778	Intermediate Similarity	NPC70595
0.7778	Intermediate Similarity	NPC123177
0.7778	Intermediate Similarity	NPC184063
0.7778	Intermediate Similarity	NPC155215
0.7778	Intermediate Similarity	NPC150978
0.7778	Intermediate Similarity	NPC193351
0.7778	Intermediate Similarity	NPC133698
0.7765	Intermediate Similarity	NPC178676
0.7753	Intermediate Similarity	NPC4986
0.7753	Intermediate Similarity	NPC38392
0.7742	Intermediate Similarity	NPC474921
0.7742	Intermediate Similarity	NPC311904
0.7727	Intermediate Similarity	NPC5130
0.7727	Intermediate Similarity	NPC475703
0.7727	Intermediate Similarity	NPC231889
0.7727	Intermediate Similarity	NPC186148
0.7717	Intermediate Similarity	NPC56369
0.7717	Intermediate Similarity	NPC475900
0.7717	Intermediate Similarity	NPC259042
0.7717	Intermediate Similarity	NPC163228
0.7717	Intermediate Similarity	NPC157686
0.7717	Intermediate Similarity	NPC476053
0.7717	Intermediate Similarity	NPC90014
0.7701	Intermediate Similarity	NPC329749
0.7701	Intermediate Similarity	NPC110405
0.7692	Intermediate Similarity	NPC472874
0.7692	Intermediate Similarity	NPC258216
0.7684	Intermediate Similarity	NPC171759
0.7683	Intermediate Similarity	NPC235906
0.7674	Intermediate Similarity	NPC245665
0.7674	Intermediate Similarity	NPC128246
0.7674	Intermediate Similarity	NPC170286
0.7667	Intermediate Similarity	NPC158488
0.7667	Intermediate Similarity	NPC253144
0.766	Intermediate Similarity	NPC23364
0.7647	Intermediate Similarity	NPC301477
0.7647	Intermediate Similarity	NPC35089
0.7647	Intermediate Similarity	NPC281949
0.7647	Intermediate Similarity	NPC25684
0.7647	Intermediate Similarity	NPC10276
0.7647	Intermediate Similarity	NPC126248
0.764	Intermediate Similarity	NPC224652
0.764	Intermediate Similarity	NPC202672
0.764	Intermediate Similarity	NPC177629
0.764	Intermediate Similarity	NPC58219
0.7634	Intermediate Similarity	NPC476009
0.7634	Intermediate Similarity	NPC93245
0.7634	Intermediate Similarity	NPC473964
0.7634	Intermediate Similarity	NPC284518
0.7619	Intermediate Similarity	NPC470244
0.7619	Intermediate Similarity	NPC470239
0.7614	Intermediate Similarity	NPC474949
0.7614	Intermediate Similarity	NPC85698
0.7614	Intermediate Similarity	NPC162071
0.7614	Intermediate Similarity	NPC474762
0.7614	Intermediate Similarity	NPC477920
0.7614	Intermediate Similarity	NPC475019
0.7614	Intermediate Similarity	NPC476015
0.7614	Intermediate Similarity	NPC9231
0.7614	Intermediate Similarity	NPC50637
0.7614	Intermediate Similarity	NPC469676
0.7609	Intermediate Similarity	NPC198853
0.7609	Intermediate Similarity	NPC24861
0.7609	Intermediate Similarity	NPC477131
0.7609	Intermediate Similarity	NPC323008
0.7609	Intermediate Similarity	NPC470010
0.7609	Intermediate Similarity	NPC262133
0.7609	Intermediate Similarity	NPC470013
0.7604	Intermediate Similarity	NPC164551
0.759	Intermediate Similarity	NPC187568
0.759	Intermediate Similarity	NPC41780
0.7586	Intermediate Similarity	NPC474780
0.7586	Intermediate Similarity	NPC472957
0.7586	Intermediate Similarity	NPC472958
0.7582	Intermediate Similarity	NPC221282
0.7582	Intermediate Similarity	NPC475925
0.7582	Intermediate Similarity	NPC284185
0.7561	Intermediate Similarity	NPC155587
0.7556	Intermediate Similarity	NPC32922
0.7556	Intermediate Similarity	NPC173926
0.7556	Intermediate Similarity	NPC151770
0.7556	Intermediate Similarity	NPC92974
0.7556	Intermediate Similarity	NPC166919

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 NPC47635 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	2134
0.2-0.3	4048
0.3-0.4	1912
0.4-0.5	517
0.5-0.6	316
0.6-0.7	34
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7753	Intermediate Similarity	NPD1695	Approved
0.7527	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1694	Approved
0.7159	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD6371	Approved
0.6737	Remote Similarity	NPD6698	Approved
0.6737	Remote Similarity	NPD46	Approved
0.6701	Remote Similarity	NPD5282	Discontinued
0.6571	Remote Similarity	NPD6686	Approved
0.6562	Remote Similarity	NPD5785	Approved
0.6538	Remote Similarity	NPD6008	Approved
0.6436	Remote Similarity	NPD4225	Approved
0.6436	Remote Similarity	NPD7638	Approved
0.6413	Remote Similarity	NPD5209	Approved
0.6373	Remote Similarity	NPD7639	Approved
0.6373	Remote Similarity	NPD7640	Approved
0.6364	Remote Similarity	NPD8039	Approved
0.6327	Remote Similarity	NPD6411	Approved
0.6316	Remote Similarity	NPD7521	Approved
0.6316	Remote Similarity	NPD7334	Approved
0.6316	Remote Similarity	NPD5330	Approved
0.6316	Remote Similarity	NPD7146	Approved
0.6316	Remote Similarity	NPD6684	Approved
0.6316	Remote Similarity	NPD6409	Approved
0.6263	Remote Similarity	NPD5778	Approved
0.6263	Remote Similarity	NPD6399	Phase 3
0.6263	Remote Similarity	NPD5779	Approved
0.6186	Remote Similarity	NPD6903	Approved
0.6186	Remote Similarity	NPD6672	Approved
0.6186	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5737	Approved
0.6182	Remote Similarity	NPD6053	Discontinued
0.6168	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5693	Phase 1
0.6162	Remote Similarity	NPD8034	Phase 2
0.6162	Remote Similarity	NPD8035	Phase 2
0.6122	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD6101	Approved
0.6117	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD3573	Approved
0.6061	Remote Similarity	NPD7838	Discovery
0.6042	Remote Similarity	NPD5363	Approved
0.604	Remote Similarity	NPD7900	Approved
0.604	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5362	Discontinued
0.6	Remote Similarity	NPD7154	Phase 3
0.6	Remote Similarity	NPD7983	Approved
0.6	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD8133	Approved
0.598	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4249	Approved
0.5979	Remote Similarity	NPD5786	Approved
0.5978	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5369	Approved
0.5943	Remote Similarity	NPD7632	Discontinued
0.5922	Remote Similarity	NPD7839	Suspended
0.5918	Remote Similarity	NPD4251	Approved
0.5918	Remote Similarity	NPD4250	Approved
0.5909	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.59	Remote Similarity	NPD5207	Approved
0.5895	Remote Similarity	NPD4269	Approved
0.5895	Remote Similarity	NPD6435	Approved
0.5895	Remote Similarity	NPD4270	Approved
0.5882	Remote Similarity	NPD7748	Approved
0.5882	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5865	Remote Similarity	NPD7902	Approved
0.5862	Remote Similarity	NPD229	Approved
0.5854	Remote Similarity	NPD7260	Phase 2
0.5842	Remote Similarity	NPD7637	Suspended
0.5826	Remote Similarity	NPD7115	Discovery
0.5825	Remote Similarity	NPD5695	Phase 3
0.5816	Remote Similarity	NPD6422	Discontinued
0.581	Remote Similarity	NPD5696	Approved
0.5806	Remote Similarity	NPD4802	Phase 2
0.5806	Remote Similarity	NPD4238	Approved
0.5806	Remote Similarity	NPD6845	Suspended
0.58	Remote Similarity	NPD6051	Approved
0.58	Remote Similarity	NPD6673	Approved
0.58	Remote Similarity	NPD6080	Approved
0.58	Remote Similarity	NPD6904	Approved
0.5789	Remote Similarity	NPD1780	Approved
0.5789	Remote Similarity	NPD1779	Approved
0.5773	Remote Similarity	NPD3668	Phase 3
0.5763	Remote Similarity	NPD8513	Phase 3
0.5763	Remote Similarity	NPD8516	Approved
0.5763	Remote Similarity	NPD8515	Approved
0.5763	Remote Similarity	NPD8517	Approved
0.5755	Remote Similarity	NPD6648	Approved
0.5743	Remote Similarity	NPD5692	Phase 3
0.5729	Remote Similarity	NPD3667	Approved
0.5728	Remote Similarity	NPD6001	Approved
0.5727	Remote Similarity	NPD5697	Approved
0.5727	Remote Similarity	NPD6412	Phase 2
0.5714	Remote Similarity	NPD6083	Phase 2
0.5714	Remote Similarity	NPD6084	Phase 2
0.5702	Remote Similarity	NPD4632	Approved
0.5702	Remote Similarity	NPD7507	Approved
0.5701	Remote Similarity	NPD5344	Discontinued
0.57	Remote Similarity	NPD5208	Approved
0.5686	Remote Similarity	NPD5694	Approved
0.5686	Remote Similarity	NPD6050	Approved
0.5686	Remote Similarity	NPD7515	Phase 2
0.5684	Remote Similarity	NPD4695	Discontinued
0.5684	Remote Similarity	NPD5368	Approved
0.5684	Remote Similarity	NPD4252	Approved
0.5684	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6881	Approved
0.5676	Remote Similarity	NPD6899	Approved
0.5676	Remote Similarity	NPD6011	Approved
0.567	Remote Similarity	NPD4788	Approved
0.5667	Remote Similarity	NPD5777	Approved
0.5664	Remote Similarity	NPD6650	Approved
0.5664	Remote Similarity	NPD6649	Approved
0.5657	Remote Similarity	NPD3618	Phase 1
0.5657	Remote Similarity	NPD6098	Approved
0.5652	Remote Similarity	NPD3702	Approved
0.5636	Remote Similarity	NPD6675	Approved
0.5636	Remote Similarity	NPD5739	Approved
0.5636	Remote Similarity	NPD7128	Approved
0.5636	Remote Similarity	NPD6402	Approved
0.563	Remote Similarity	NPD8267	Approved
0.563	Remote Similarity	NPD8269	Approved
0.563	Remote Similarity	NPD8266	Approved
0.563	Remote Similarity	NPD8268	Approved
0.5625	Remote Similarity	NPD6012	Approved
0.5625	Remote Similarity	NPD6372	Approved
0.5625	Remote Similarity	NPD6373	Approved
0.5625	Remote Similarity	NPD6013	Approved
0.5625	Remote Similarity	NPD6014	Approved
0.5625	Remote Similarity	NPD9298	Approved
0.5619	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD3665	Phase 1
0.5612	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD3666	Approved
0.5612	Remote Similarity	NPD3133	Approved
0.5612	Remote Similarity	NPD4786	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