NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	460.25
Volume:	484.216
LogP:	2.997
LogD:	1.91
LogS:	-4.04
# Rotatable Bonds:	12
TPSA:	106.97
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.302
Synthetic Accessibility Score:	5.316
Fsp3:	0.615
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.897
MDCK Permeability:	4.0334853110834956e-05
Pgp-inhibitor:	0.343
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.103
20% Bioavailability (F20%):	0.19
30% Bioavailability (F30%):	0.105

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.925
Plasma Protein Binding (PPB):	69.66716003417969%
Volume Distribution (VD):	1.893
Pgp-substrate:	44.5880126953125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.089
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.128
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.735
CYP3A4-substrate:	0.303

ADMET: Excretion

Clearance (CL):	4.61
Half-life (T1/2):	0.84

ADMET: Toxicity

hERG Blockers:	0.427
Human Hepatotoxicity (H-HT):	0.834
Drug-inuced Liver Injury (DILI):	0.35
AMES Toxicity:	0.838
Rat Oral Acute Toxicity:	0.827
Maximum Recommended Daily Dose:	0.942
Skin Sensitization:	0.974
Carcinogencity:	0.829
Eye Corrosion:	0.031
Eye Irritation:	0.014
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC476801

Natural Product ID:	NPC476801
*Common Name:**	caseanigrescen A-2
IUPAC Name:	[(2R,4aS,5R,6R,7S,8S,8aS)-6-acetyloxy-4,4a-diformyl-5-hydroxy-7,8-dimethyl-8-(3-methylidenepent-4-enyl)-1,2,5,6,7,8a-hexahydronaphthalen-2-yl] butanoate
Synonyms:	Caseanigrescen A-2
Standard InCHIKey:	SIFNZKURRCNDHK-CWWYLWEJSA-N
Standard InCHI:	InChI=1S/C26H36O7/c1-7-9-22(30)33-20-12-19(14-27)26(15-28)21(13-20)25(6,11-10-16(3)8-2)17(4)23(24(26)31)32-18(5)29/h8,12,14-15,17,20-21,23-24,31H,2-3,7,9-11,13H2,1,4-6H3/t17-,20+,21+,23-,24+,25-,26+/m1/s1
SMILES:	CCCC(=O)O[C@@H]1C[C@H]2[C@]([C@@H]([C@H]([C@@H]([C@]2(C(=C1)C=O)C=O)O)OC(=O)C)C)(C)CCC(=C)C=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	16109793
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO31135	Casearia nigrescens	Species	Salicaceae	Eukaryota	n.a.	flower	n.a.	PMID[17315961]
NPO31135	Casearia nigrescens	Species	Salicaceae	Eukaryota	leaves and flowers	Zahamena region of Madagascar, Toamasina, 3 km northeast of Nosivola (1741'01?S, 4838'28?)	2001-NOV	PMID[17315961]
NPO31135	Casearia nigrescens	Species	Salicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17315961]

☑ 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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	3500	nM	PMID[17315961]

☑ 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 NPC476801 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	230
0.1-0.2	1222
0.2-0.3	3714
0.3-0.4	6335
0.4-0.5	12205
0.5-0.6	10159
0.6-0.7	6602
0.7-0.8	2147
0.8-0.85	73
0.85-0.9	6
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9612	High Similarity	NPC476802
0.9612	High Similarity	NPC89171
0.9135	High Similarity	NPC470297
0.8673	High Similarity	NPC284707
0.8596	High Similarity	NPC473636
0.8596	High Similarity	NPC77689
0.8584	High Similarity	NPC53396
0.8584	High Similarity	NPC98249
0.8584	High Similarity	NPC134430
0.8559	High Similarity	NPC269530
0.8482	Intermediate Similarity	NPC469496
0.8482	Intermediate Similarity	NPC471204
0.8482	Intermediate Similarity	NPC56448
0.8482	Intermediate Similarity	NPC469463
0.8482	Intermediate Similarity	NPC469454
0.8468	Intermediate Similarity	NPC188738
0.8462	Intermediate Similarity	NPC11895
0.8435	Intermediate Similarity	NPC473839
0.8435	Intermediate Similarity	NPC211093
0.8421	Intermediate Similarity	NPC284068
0.8421	Intermediate Similarity	NPC469684
0.8421	Intermediate Similarity	NPC475809
0.8393	Intermediate Similarity	NPC277769
0.839	Intermediate Similarity	NPC81736
0.839	Intermediate Similarity	NPC172154
0.8378	Intermediate Similarity	NPC5103
0.8376	Intermediate Similarity	NPC170538
0.8364	Intermediate Similarity	NPC306265
0.8364	Intermediate Similarity	NPC189075
0.8364	Intermediate Similarity	NPC275539
0.8364	Intermediate Similarity	NPC151393
0.8362	Intermediate Similarity	NPC476961
0.8349	Intermediate Similarity	NPC469607
0.8349	Intermediate Similarity	NPC102352
0.8349	Intermediate Similarity	NPC1679
0.8333	Intermediate Similarity	NPC282233
0.8333	Intermediate Similarity	NPC95585
0.8333	Intermediate Similarity	NPC99266
0.8333	Intermediate Similarity	NPC159533
0.8319	Intermediate Similarity	NPC293112
0.8318	Intermediate Similarity	NPC303559
0.8318	Intermediate Similarity	NPC471412
0.8305	Intermediate Similarity	NPC469789
0.8304	Intermediate Similarity	NPC179798
0.8304	Intermediate Similarity	NPC304180
0.8302	Intermediate Similarity	NPC23364
0.8288	Intermediate Similarity	NPC474243
0.8273	Intermediate Similarity	NPC110496
0.8273	Intermediate Similarity	NPC230541
0.8261	Intermediate Similarity	NPC473968
0.8261	Intermediate Similarity	NPC474518
0.8257	Intermediate Similarity	NPC296950
0.8257	Intermediate Similarity	NPC146731
0.8246	Intermediate Similarity	NPC238667
0.8241	Intermediate Similarity	NPC137430
0.8241	Intermediate Similarity	NPC295791
0.8235	Intermediate Similarity	NPC8369
0.823	Intermediate Similarity	NPC90952
0.823	Intermediate Similarity	NPC4573
0.8224	Intermediate Similarity	NPC471413
0.822	Intermediate Similarity	NPC269642
0.8214	Intermediate Similarity	NPC286880
0.8214	Intermediate Similarity	NPC210005
0.8198	Intermediate Similarity	NPC277017
0.8198	Intermediate Similarity	NPC37628
0.8198	Intermediate Similarity	NPC154608
0.8198	Intermediate Similarity	NPC192813
0.819	Intermediate Similarity	NPC183012
0.8174	Intermediate Similarity	NPC268954
0.8174	Intermediate Similarity	NPC44170
0.8174	Intermediate Similarity	NPC196931
0.8167	Intermediate Similarity	NPC473635
0.8165	Intermediate Similarity	NPC264048
0.8165	Intermediate Similarity	NPC95899
0.8165	Intermediate Similarity	NPC120321
0.8165	Intermediate Similarity	NPC8196
0.8165	Intermediate Similarity	NPC156681
0.8165	Intermediate Similarity	NPC23584
0.8158	Intermediate Similarity	NPC478212
0.8151	Intermediate Similarity	NPC67251
0.8151	Intermediate Similarity	NPC120724
0.8148	Intermediate Similarity	NPC97435
0.8142	Intermediate Similarity	NPC317107
0.8142	Intermediate Similarity	NPC247031
0.8142	Intermediate Similarity	NPC97939
0.8142	Intermediate Similarity	NPC132790
0.8142	Intermediate Similarity	NPC324683
0.8142	Intermediate Similarity	NPC100329
0.8136	Intermediate Similarity	NPC67569
0.8136	Intermediate Similarity	NPC46570
0.8125	Intermediate Similarity	NPC153239
0.8125	Intermediate Similarity	NPC478210
0.8125	Intermediate Similarity	NPC141350
0.8125	Intermediate Similarity	NPC475065
0.812	Intermediate Similarity	NPC475775
0.812	Intermediate Similarity	NPC475041
0.812	Intermediate Similarity	NPC476529
0.8115	Intermediate Similarity	NPC231529
0.8108	Intermediate Similarity	NPC284732
0.8108	Intermediate Similarity	NPC112780
0.8108	Intermediate Similarity	NPC3316
0.8108	Intermediate Similarity	NPC143609
0.8108	Intermediate Similarity	NPC187435
0.8108	Intermediate Similarity	NPC329048
0.8108	Intermediate Similarity	NPC133422
0.8108	Intermediate Similarity	NPC67321
0.8108	Intermediate Similarity	NPC144854
0.8108	Intermediate Similarity	NPC330011
0.8108	Intermediate Similarity	NPC78966
0.8103	Intermediate Similarity	NPC470959
0.8103	Intermediate Similarity	NPC23046
0.8103	Intermediate Similarity	NPC478204
0.8103	Intermediate Similarity	NPC476965
0.8103	Intermediate Similarity	NPC476959
0.8103	Intermediate Similarity	NPC58662
0.8095	Intermediate Similarity	NPC250075
0.8095	Intermediate Similarity	NPC470697
0.8091	Intermediate Similarity	NPC118911
0.8087	Intermediate Similarity	NPC110861
0.8087	Intermediate Similarity	NPC147912
0.8087	Intermediate Similarity	NPC67259
0.8087	Intermediate Similarity	NPC117712
0.8083	Intermediate Similarity	NPC24651
0.8083	Intermediate Similarity	NPC470922
0.8073	Intermediate Similarity	NPC31058
0.8073	Intermediate Similarity	NPC469606
0.8073	Intermediate Similarity	NPC162973
0.8073	Intermediate Similarity	NPC11956
0.8073	Intermediate Similarity	NPC273005
0.8073	Intermediate Similarity	NPC80781
0.807	Intermediate Similarity	NPC317687
0.807	Intermediate Similarity	NPC472002
0.807	Intermediate Similarity	NPC12046
0.807	Intermediate Similarity	NPC194951
0.8067	Intermediate Similarity	NPC23786
0.8067	Intermediate Similarity	NPC107493
0.8067	Intermediate Similarity	NPC470265
0.8056	Intermediate Similarity	NPC174314
0.8056	Intermediate Similarity	NPC476299
0.8056	Intermediate Similarity	NPC474012
0.8053	Intermediate Similarity	NPC478211
0.8053	Intermediate Similarity	NPC235014
0.8051	Intermediate Similarity	NPC48692
0.8051	Intermediate Similarity	NPC107338
0.8051	Intermediate Similarity	NPC109607
0.8051	Intermediate Similarity	NPC476962
0.8051	Intermediate Similarity	NPC475885
0.8037	Intermediate Similarity	NPC73911
0.8037	Intermediate Similarity	NPC17326
0.8037	Intermediate Similarity	NPC134454
0.8036	Intermediate Similarity	NPC476479
0.8036	Intermediate Similarity	NPC469916
0.8036	Intermediate Similarity	NPC472439
0.8036	Intermediate Similarity	NPC475418
0.8036	Intermediate Similarity	NPC318363
0.8036	Intermediate Similarity	NPC473482
0.8034	Intermediate Similarity	NPC478206
0.8034	Intermediate Similarity	NPC108581
0.8034	Intermediate Similarity	NPC124676
0.8034	Intermediate Similarity	NPC146280
0.8034	Intermediate Similarity	NPC251310
0.8034	Intermediate Similarity	NPC478205
0.8018	Intermediate Similarity	NPC80566
0.8018	Intermediate Similarity	NPC477125
0.8018	Intermediate Similarity	NPC111952
0.8017	Intermediate Similarity	NPC176840
0.8017	Intermediate Similarity	NPC64318
0.8017	Intermediate Similarity	NPC207217
0.8017	Intermediate Similarity	NPC478216
0.8017	Intermediate Similarity	NPC190286
0.8017	Intermediate Similarity	NPC471816
0.8	Intermediate Similarity	NPC105926
0.8	Intermediate Similarity	NPC475966
0.8	Intermediate Similarity	NPC157441
0.8	Intermediate Similarity	NPC194273
0.8	Intermediate Similarity	NPC18945
0.8	Intermediate Similarity	NPC91693
0.8	Intermediate Similarity	NPC477126
0.8	Intermediate Similarity	NPC25909
0.8	Intermediate Similarity	NPC265557
0.8	Intermediate Similarity	NPC254202
0.7984	Intermediate Similarity	NPC477195
0.7982	Intermediate Similarity	NPC469655
0.7982	Intermediate Similarity	NPC111292
0.7982	Intermediate Similarity	NPC474846
0.7982	Intermediate Similarity	NPC469656
0.7982	Intermediate Similarity	NPC308824
0.7966	Intermediate Similarity	NPC236918
0.7966	Intermediate Similarity	NPC470186
0.7966	Intermediate Similarity	NPC476960
0.7966	Intermediate Similarity	NPC156745
0.7965	Intermediate Similarity	NPC469370
0.7965	Intermediate Similarity	NPC310546
0.7963	Intermediate Similarity	NPC124512
0.7963	Intermediate Similarity	NPC316598
0.7963	Intermediate Similarity	NPC471932
0.7963	Intermediate Similarity	NPC159763
0.7963	Intermediate Similarity	NPC216478
0.7963	Intermediate Similarity	NPC278386
0.7961	Intermediate Similarity	NPC473229

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 NPC476801 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1518
0.2-0.3	3433
0.3-0.4	2393
0.4-0.5	1046
0.5-0.6	355
0.6-0.7	178
0.7-0.8	21
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
0.7963	Intermediate Similarity	NPD4225	Approved
0.7949	Intermediate Similarity	NPD7115	Discovery
0.7719	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD5779	Approved
0.7664	Intermediate Similarity	NPD5778	Approved
0.7636	Intermediate Similarity	NPD7638	Approved
0.7568	Intermediate Similarity	NPD7640	Approved
0.7568	Intermediate Similarity	NPD7639	Approved
0.754	Intermediate Similarity	NPD7319	Approved
0.75	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6319	Approved
0.744	Intermediate Similarity	NPD7507	Approved
0.7436	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD6686	Approved
0.7407	Intermediate Similarity	NPD6411	Approved
0.7395	Intermediate Similarity	NPD4632	Approved
0.7345	Intermediate Similarity	NPD5344	Discontinued
0.728	Intermediate Similarity	NPD8328	Phase 3
0.7258	Intermediate Similarity	NPD8517	Approved
0.7258	Intermediate Similarity	NPD8516	Approved
0.7258	Intermediate Similarity	NPD8513	Phase 3
0.7258	Intermediate Similarity	NPD8515	Approved
0.7248	Intermediate Similarity	NPD7983	Approved
0.7232	Intermediate Similarity	NPD7902	Approved
0.7227	Intermediate Similarity	NPD6649	Approved
0.7227	Intermediate Similarity	NPD6650	Approved
0.7222	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6101	Approved
0.7222	Intermediate Similarity	NPD7492	Approved
0.7179	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD6054	Approved
0.717	Intermediate Similarity	NPD1694	Approved
0.7167	Intermediate Similarity	NPD8297	Approved
0.7165	Intermediate Similarity	NPD6616	Approved
0.7156	Intermediate Similarity	NPD46	Approved
0.7156	Intermediate Similarity	NPD6698	Approved
0.7143	Intermediate Similarity	NPD6371	Approved
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7119	Intermediate Similarity	NPD6899	Approved
0.7119	Intermediate Similarity	NPD6881	Approved
0.7117	Intermediate Similarity	NPD7748	Approved
0.7109	Intermediate Similarity	NPD7078	Approved
0.7105	Intermediate Similarity	NPD6648	Approved
0.7091	Intermediate Similarity	NPD7515	Phase 2
0.7091	Intermediate Similarity	NPD6079	Approved
0.7073	Intermediate Similarity	NPD6009	Approved
0.7073	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6370	Approved
0.7059	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6373	Approved
0.7059	Intermediate Similarity	NPD6372	Approved
0.7054	Intermediate Similarity	NPD7736	Approved
0.7054	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD5697	Approved
0.7027	Intermediate Similarity	NPD6399	Phase 3
0.7023	Intermediate Similarity	NPD7260	Phase 2
0.7018	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD7604	Phase 2
0.7	Intermediate Similarity	NPD7102	Approved
0.7	Intermediate Similarity	NPD7838	Discovery
0.7	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD5785	Approved
0.7	Intermediate Similarity	NPD6883	Approved
0.7	Intermediate Similarity	NPD4634	Approved
0.6984	Remote Similarity	NPD6015	Approved
0.6984	Remote Similarity	NPD5983	Phase 2
0.6984	Remote Similarity	NPD6921	Approved
0.6984	Remote Similarity	NPD6016	Approved
0.6983	Remote Similarity	NPD7632	Discontinued
0.6977	Remote Similarity	NPD8074	Phase 3
0.6975	Remote Similarity	NPD6011	Approved
0.6964	Remote Similarity	NPD7900	Approved
0.6964	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7128	Approved
0.6949	Remote Similarity	NPD6675	Approved
0.6949	Remote Similarity	NPD6008	Approved
0.6949	Remote Similarity	NPD6402	Approved
0.6949	Remote Similarity	NPD5739	Approved
0.6942	Remote Similarity	NPD6869	Approved
0.6942	Remote Similarity	NPD6847	Approved
0.6942	Remote Similarity	NPD6617	Approved
0.6942	Remote Similarity	NPD8130	Phase 1
0.6929	Remote Similarity	NPD5988	Approved
0.6917	Remote Similarity	NPD6013	Approved
0.6917	Remote Similarity	NPD6014	Approved
0.6917	Remote Similarity	NPD6012	Approved
0.6909	Remote Similarity	NPD5328	Approved
0.6905	Remote Similarity	NPD6059	Approved
0.6899	Remote Similarity	NPD6336	Discontinued
0.6891	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6053	Discontinued
0.6885	Remote Similarity	NPD6882	Approved
0.6881	Remote Similarity	NPD3573	Approved
0.685	Remote Similarity	NPD7503	Approved
0.6846	Remote Similarity	NPD8293	Discontinued
0.6842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5222	Approved
0.6842	Remote Similarity	NPD5221	Approved
0.6833	Remote Similarity	NPD7320	Approved
0.6789	Remote Similarity	NPD3618	Phase 1
0.6786	Remote Similarity	NPD7637	Suspended
0.6783	Remote Similarity	NPD5173	Approved
0.675	Remote Similarity	NPD5701	Approved
0.675	Remote Similarity	NPD6412	Phase 2
0.672	Remote Similarity	NPD6868	Approved
0.6695	Remote Similarity	NPD5211	Phase 2
0.6693	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD5786	Approved
0.6614	Remote Similarity	NPD6335	Approved
0.6614	Remote Similarity	NPD7327	Approved
0.6614	Remote Similarity	NPD7328	Approved
0.661	Remote Similarity	NPD5223	Approved
0.6593	Remote Similarity	NPD6845	Suspended
0.6589	Remote Similarity	NPD8033	Approved
0.6583	Remote Similarity	NPD5141	Approved
0.6562	Remote Similarity	NPD7101	Approved
0.6562	Remote Similarity	NPD7100	Approved
0.6555	Remote Similarity	NPD4633	Approved
0.6555	Remote Similarity	NPD5225	Approved
0.6555	Remote Similarity	NPD5224	Approved
0.6555	Remote Similarity	NPD5226	Approved
0.6552	Remote Similarity	NPD7839	Suspended
0.6545	Remote Similarity	NPD5363	Approved
0.6541	Remote Similarity	NPD6033	Approved
0.6535	Remote Similarity	NPD6317	Approved
0.6522	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD8451	Approved
0.6512	Remote Similarity	NPD8294	Approved
0.6512	Remote Similarity	NPD8377	Approved
0.65	Remote Similarity	NPD5174	Approved
0.65	Remote Similarity	NPD5175	Approved
0.6496	Remote Similarity	NPD6083	Phase 2
0.6496	Remote Similarity	NPD6084	Phase 2
0.6496	Remote Similarity	NPD4755	Approved
0.6491	Remote Similarity	NPD8034	Phase 2
0.6491	Remote Similarity	NPD8035	Phase 2
0.6489	Remote Similarity	NPD7642	Approved
0.6489	Remote Similarity	NPD7829	Approved
0.6489	Remote Similarity	NPD7830	Approved
0.6486	Remote Similarity	NPD7334	Approved
0.6486	Remote Similarity	NPD5330	Approved
0.6486	Remote Similarity	NPD7146	Approved
0.6486	Remote Similarity	NPD7521	Approved
0.6486	Remote Similarity	NPD6684	Approved
0.6486	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6409	Approved
0.6484	Remote Similarity	NPD6313	Approved
0.6484	Remote Similarity	NPD6314	Approved
0.6466	Remote Similarity	NPD8448	Approved
0.6462	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6462	Remote Similarity	NPD8296	Approved
0.6462	Remote Similarity	NPD8378	Approved
0.6462	Remote Similarity	NPD8380	Approved
0.6462	Remote Similarity	NPD8335	Approved
0.6462	Remote Similarity	NPD8379	Approved
0.6457	Remote Similarity	NPD6274	Approved
0.6455	Remote Similarity	NPD4786	Approved
0.6429	Remote Similarity	NPD8133	Approved
0.6422	Remote Similarity	NPD3667	Approved
0.64	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD4700	Approved
0.6381	Remote Similarity	NPD8039	Approved
0.6379	Remote Similarity	NPD5282	Discontinued
0.6372	Remote Similarity	NPD6672	Approved
0.6372	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD5737	Approved
0.6372	Remote Similarity	NPD6903	Approved
0.6364	Remote Similarity	NPD6110	Phase 1
0.6357	Remote Similarity	NPD7641	Discontinued
0.6348	Remote Similarity	NPD5281	Approved
0.6348	Remote Similarity	NPD5284	Approved
0.6325	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD5695	Phase 3
0.6324	Remote Similarity	NPD8391	Approved
0.6324	Remote Similarity	NPD8392	Approved
0.6324	Remote Similarity	NPD8390	Approved
0.6316	Remote Similarity	NPD8341	Approved
0.6316	Remote Similarity	NPD8340	Approved
0.6316	Remote Similarity	NPD8342	Approved
0.6316	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8299	Approved
0.6306	Remote Similarity	NPD3666	Approved
0.6306	Remote Similarity	NPD3133	Approved
0.6306	Remote Similarity	NPD3665	Phase 1
0.6303	Remote Similarity	NPD5696	Approved
0.6293	Remote Similarity	NPD4202	Approved
0.629	Remote Similarity	NPD4730	Approved
0.629	Remote Similarity	NPD4729	Approved
0.629	Remote Similarity	NPD5168	Approved
0.6283	Remote Similarity	NPD7524	Approved
0.6273	Remote Similarity	NPD4269	Approved
0.6273	Remote Similarity	NPD4270	Approved
0.6273	Remote Similarity	NPD5209	Approved
0.625	Remote Similarity	NPD7520	Clinical (unspecified phase)

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