NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	453.29
Volume:	477.117
LogP:	4.753
LogD:	3.969
LogS:	-5.155
# Rotatable Bonds:	2
TPSA:	64.63
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	5.759
Fsp3:	0.786
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.79
MDCK Permeability:	1.7573982404428534e-05
Pgp-inhibitor:	0.209
Pgp-substrate:	0.347
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.048

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.345
Plasma Protein Binding (PPB):	77.85118865966797%
Volume Distribution (VD):	2.072
Pgp-substrate:	8.345246315002441%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.126
CYP2C19-inhibitor:	0.427
CYP2C19-substrate:	0.844
CYP2C9-inhibitor:	0.183
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.563
CYP2D6-substrate:	0.874
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.488

ADMET: Excretion

Clearance (CL):	4.126
Half-life (T1/2):	0.068

ADMET: Toxicity

hERG Blockers:	0.612
Human Hepatotoxicity (H-HT):	0.414
Drug-inuced Liver Injury (DILI):	0.387
AMES Toxicity:	0.459
Rat Oral Acute Toxicity:	0.879
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.935
Carcinogencity:	0.953
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC478136

Natural Product ID:	NPC478136
*Common Name:**	Formic acid 11-oxo-17,23beta-epoxyveratraman-3beta-yl ester
IUPAC Name:	[(3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b-tetramethyl-11-oxospiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-yl] formate
Synonyms:
Standard InCHIKey:	RSRKUUDRGRLQRU-AROXZRCDSA-N
Standard InCHI:	InChI=1S/C28H39NO4/c1-15-11-22-25(29-13-15)17(3)28(33-22)10-8-20-21-6-5-18-12-19(32-14-30)7-9-27(18,4)24(21)26(31)23(20)16(28)2/h5,14-15,17,19-22,24-25,29H,6-13H2,1-4H3/t15-,17+,19-,20-,21-,22+,24+,25-,27-,28-/m0/s1
SMILES:	C[C@H]1C[C@@H]2[C@H]([C@H]([C@]3(O2)CC[C@H]4[C@@H]5CC=C6C[C@H](CC[C@@]6([C@H]5C(=O)C4=C3C)C)OC=O)C)NC1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122178946
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002724] Steroidal alkaloids [CHEMONTID:0002728] Jerveratrum-type 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
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	roots and rhizomes	n.a.	n.a.	PMID[25835537]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15848	Veratrum nigrum	Species	Melanthiaceae	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
IC50	1
Others	2

Activity Type	# Activity
Cell Line	2
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2219	Cell Line	C2C12	Mus musculus	Activity	=	49.9	%	PMID[25835537]
NPT2219	Cell Line	C2C12	Mus musculus	Activity	=	15	%	PMID[25835537]
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	11300	nM	PMID[25835537]

☑ 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 NPC478136 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	120
0.1-0.2	834
0.2-0.3	3939
0.3-0.4	18431
0.4-0.5	11723
0.5-0.6	7035
0.6-0.7	595
0.7-0.8	14
0.8-0.85	3
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9256	High Similarity	NPC317654
0.9256	High Similarity	NPC96010
0.8438	Intermediate Similarity	NPC478139
0.843	Intermediate Similarity	NPC304646
0.843	Intermediate Similarity	NPC28280
0.7721	Intermediate Similarity	NPC297058
0.7686	Intermediate Similarity	NPC233256
0.7686	Intermediate Similarity	NPC195841
0.7661	Intermediate Similarity	NPC79238
0.7481	Intermediate Similarity	NPC478138
0.7381	Intermediate Similarity	NPC474459
0.7323	Intermediate Similarity	NPC474452
0.7302	Intermediate Similarity	NPC472313
0.7273	Intermediate Similarity	NPC239768
0.7273	Intermediate Similarity	NPC128698
0.7266	Intermediate Similarity	NPC478137
0.7258	Intermediate Similarity	NPC86906
0.7252	Intermediate Similarity	NPC35037
0.7087	Intermediate Similarity	NPC147835
0.7087	Intermediate Similarity	NPC95920
0.7087	Intermediate Similarity	NPC85001
0.7087	Intermediate Similarity	NPC253645
0.704	Intermediate Similarity	NPC475239
0.7031	Intermediate Similarity	NPC63511
0.7016	Intermediate Similarity	NPC176012
0.6978	Remote Similarity	NPC201359
0.6967	Remote Similarity	NPC474164
0.6953	Remote Similarity	NPC218602
0.6905	Remote Similarity	NPC477000
0.6905	Remote Similarity	NPC477001
0.6899	Remote Similarity	NPC473040
0.6861	Remote Similarity	NPC321197
0.6833	Remote Similarity	NPC190442
0.68	Remote Similarity	NPC310981
0.6791	Remote Similarity	NPC470276
0.6791	Remote Similarity	NPC9714
0.6777	Remote Similarity	NPC229976
0.6774	Remote Similarity	NPC252295
0.6772	Remote Similarity	NPC119329
0.6765	Remote Similarity	NPC470277
0.675	Remote Similarity	NPC84171
0.6744	Remote Similarity	NPC177064
0.672	Remote Similarity	NPC470906
0.6719	Remote Similarity	NPC60681
0.6695	Remote Similarity	NPC470051
0.6695	Remote Similarity	NPC470050
0.6693	Remote Similarity	NPC470954
0.669	Remote Similarity	NPC139585
0.6642	Remote Similarity	NPC470538
0.6641	Remote Similarity	NPC212874
0.6641	Remote Similarity	NPC189616
0.6619	Remote Similarity	NPC296686
0.6614	Remote Similarity	NPC185530
0.6613	Remote Similarity	NPC307164
0.6599	Remote Similarity	NPC180770
0.6599	Remote Similarity	NPC302276
0.6593	Remote Similarity	NPC470275
0.6591	Remote Similarity	NPC470960
0.6589	Remote Similarity	NPC93179
0.6567	Remote Similarity	NPC135431
0.6567	Remote Similarity	NPC474181
0.6565	Remote Similarity	NPC470536
0.6562	Remote Similarity	NPC180204
0.6562	Remote Similarity	NPC26478
0.6562	Remote Similarity	NPC98765
0.6562	Remote Similarity	NPC36688
0.6562	Remote Similarity	NPC176883
0.6562	Remote Similarity	NPC112009
0.656	Remote Similarity	NPC110937
0.656	Remote Similarity	NPC10057
0.656	Remote Similarity	NPC151488
0.6544	Remote Similarity	NPC475913
0.6544	Remote Similarity	NPC473720
0.6541	Remote Similarity	NPC124358
0.6538	Remote Similarity	NPC476958
0.6538	Remote Similarity	NPC91034
0.6538	Remote Similarity	NPC46981
0.6536	Remote Similarity	NPC298005
0.6536	Remote Similarity	NPC36463
0.6532	Remote Similarity	NPC474909
0.6532	Remote Similarity	NPC33473
0.6531	Remote Similarity	NPC287885
0.6529	Remote Similarity	NPC177141
0.6529	Remote Similarity	NPC288699
0.6519	Remote Similarity	NPC209252
0.6515	Remote Similarity	NPC37116
0.6515	Remote Similarity	NPC473627
0.6513	Remote Similarity	NPC61717
0.6513	Remote Similarity	NPC201899
0.6513	Remote Similarity	NPC471674
0.6513	Remote Similarity	NPC244380
0.6512	Remote Similarity	NPC133420
0.6512	Remote Similarity	NPC75523
0.6512	Remote Similarity	NPC44514
0.651	Remote Similarity	NPC162910
0.6508	Remote Similarity	NPC91604
0.6508	Remote Similarity	NPC176845
0.6496	Remote Similarity	NPC475834
0.6496	Remote Similarity	NPC475520
0.6496	Remote Similarity	NPC474179
0.6493	Remote Similarity	NPC122056
0.6489	Remote Similarity	NPC470535
0.6484	Remote Similarity	NPC475320
0.6483	Remote Similarity	NPC477072
0.648	Remote Similarity	NPC322063
0.648	Remote Similarity	NPC328371
0.648	Remote Similarity	NPC289140
0.6475	Remote Similarity	NPC212679
0.6475	Remote Similarity	NPC220454
0.6475	Remote Similarity	NPC273199
0.6475	Remote Similarity	NPC469595
0.6471	Remote Similarity	NPC75810
0.6471	Remote Similarity	NPC39485
0.6471	Remote Similarity	NPC221196
0.6471	Remote Similarity	NPC470048
0.6462	Remote Similarity	NPC127790
0.6462	Remote Similarity	NPC230677
0.6458	Remote Similarity	NPC25455
0.6458	Remote Similarity	NPC15249
0.6457	Remote Similarity	NPC476303
0.6457	Remote Similarity	NPC201406
0.6454	Remote Similarity	NPC237286
0.6452	Remote Similarity	NPC38830
0.6452	Remote Similarity	NPC471720
0.6449	Remote Similarity	NPC474585
0.6446	Remote Similarity	NPC226863
0.6444	Remote Similarity	NPC147912
0.6444	Remote Similarity	NPC67259
0.6444	Remote Similarity	NPC470953
0.6441	Remote Similarity	NPC470047
0.6441	Remote Similarity	NPC470046
0.6439	Remote Similarity	NPC175585
0.6434	Remote Similarity	NPC471364
0.6434	Remote Similarity	NPC476237
0.6434	Remote Similarity	NPC471365
0.6434	Remote Similarity	NPC254202
0.6434	Remote Similarity	NPC132395
0.6429	Remote Similarity	NPC84335
0.6429	Remote Similarity	NPC291634
0.6429	Remote Similarity	NPC38530
0.6429	Remote Similarity	NPC320306
0.6429	Remote Similarity	NPC292133
0.6429	Remote Similarity	NPC253826
0.6429	Remote Similarity	NPC126815
0.6424	Remote Similarity	NPC298469
0.6424	Remote Similarity	NPC141669
0.6423	Remote Similarity	NPC49420
0.6423	Remote Similarity	NPC218301
0.6423	Remote Similarity	NPC26888
0.6418	Remote Similarity	NPC191620
0.6418	Remote Similarity	NPC236217
0.6417	Remote Similarity	NPC220478
0.6414	Remote Similarity	NPC122819
0.6412	Remote Similarity	NPC475294
0.6412	Remote Similarity	NPC144459
0.6408	Remote Similarity	NPC204556
0.6406	Remote Similarity	NPC99411
0.6406	Remote Similarity	NPC474348
0.6406	Remote Similarity	NPC168319
0.6406	Remote Similarity	NPC194028
0.6403	Remote Similarity	NPC476504
0.64	Remote Similarity	NPC470016
0.64	Remote Similarity	NPC318282
0.64	Remote Similarity	NPC317586
0.64	Remote Similarity	NPC281134
0.64	Remote Similarity	NPC171395
0.64	Remote Similarity	NPC173875
0.64	Remote Similarity	NPC174948
0.64	Remote Similarity	NPC127197
0.64	Remote Similarity	NPC469995
0.64	Remote Similarity	NPC174117
0.6397	Remote Similarity	NPC190286
0.6393	Remote Similarity	NPC73995
0.6391	Remote Similarity	NPC72753
0.6391	Remote Similarity	NPC163314
0.6391	Remote Similarity	NPC29133
0.6387	Remote Similarity	NPC100391
0.6385	Remote Similarity	NPC87919
0.6385	Remote Similarity	NPC472868
0.6383	Remote Similarity	NPC476503
0.6382	Remote Similarity	NPC214821
0.6382	Remote Similarity	NPC298067
0.6378	Remote Similarity	NPC478056
0.6378	Remote Similarity	NPC98868
0.6378	Remote Similarity	NPC92275
0.6376	Remote Similarity	NPC478140
0.6371	Remote Similarity	NPC475657
0.6371	Remote Similarity	NPC93027
0.637	Remote Similarity	NPC473535
0.637	Remote Similarity	NPC147753
0.637	Remote Similarity	NPC150057
0.6364	Remote Similarity	NPC220730
0.6364	Remote Similarity	NPC61411
0.6364	Remote Similarity	NPC220155
0.6358	Remote Similarity	NPC803
0.6357	Remote Similarity	NPC308726
0.6357	Remote Similarity	NPC119601
0.6357	Remote Similarity	NPC114540
0.6357	Remote Similarity	NPC32577
0.6357	Remote Similarity	NPC155332

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 NPC478136 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	94
0.1-0.2	508
0.2-0.3	2465
0.3-0.4	4088
0.4-0.5	1505
0.5-0.6	449
0.6-0.7	41
0.7-0.8	0
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
0.6923	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7336	Phase 2
0.6923	Remote Similarity	NPD7335	Phase 2
0.6765	Remote Similarity	NPD6908	Approved
0.6765	Remote Similarity	NPD6909	Approved
0.6748	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.662	Remote Similarity	NPD6914	Discontinued
0.6596	Remote Similarity	NPD8336	Approved
0.6596	Remote Similarity	NPD8337	Approved
0.6547	Remote Similarity	NPD7122	Discontinued
0.6528	Remote Similarity	NPD6845	Suspended
0.6414	Remote Similarity	NPD8338	Approved
0.6414	Remote Similarity	NPD8449	Approved
0.64	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.637	Remote Similarity	NPD8450	Suspended
0.635	Remote Similarity	NPD7115	Discovery
0.6345	Remote Similarity	NPD7260	Phase 2
0.6336	Remote Similarity	NPD6008	Approved
0.6311	Remote Similarity	NPD6903	Approved
0.6311	Remote Similarity	NPD5737	Approved
0.6311	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6672	Approved
0.629	Remote Similarity	NPD5693	Phase 1
0.6281	Remote Similarity	NPD5330	Approved
0.6281	Remote Similarity	NPD6684	Approved
0.6281	Remote Similarity	NPD6409	Approved
0.6281	Remote Similarity	NPD7146	Approved
0.6281	Remote Similarity	NPD7334	Approved
0.6281	Remote Similarity	NPD7521	Approved
0.624	Remote Similarity	NPD6399	Phase 3
0.6212	Remote Similarity	NPD6920	Discontinued
0.621	Remote Similarity	NPD5207	Approved
0.616	Remote Similarity	NPD6050	Approved
0.6143	Remote Similarity	NPD7517	Approved
0.6143	Remote Similarity	NPD7519	Approved
0.6143	Remote Similarity	NPD7518	Approved
0.6142	Remote Similarity	NPD5695	Phase 3
0.6129	Remote Similarity	NPD6904	Approved
0.6129	Remote Similarity	NPD6080	Approved
0.6129	Remote Similarity	NPD6673	Approved
0.6124	Remote Similarity	NPD7638	Approved
0.6119	Remote Similarity	NPD7320	Approved
0.6111	Remote Similarity	NPD7507	Approved
0.609	Remote Similarity	NPD7128	Approved
0.609	Remote Similarity	NPD6675	Approved
0.609	Remote Similarity	NPD5739	Approved
0.609	Remote Similarity	NPD6402	Approved
0.608	Remote Similarity	NPD5692	Phase 3
0.6077	Remote Similarity	NPD7639	Approved
0.6077	Remote Similarity	NPD7640	Approved
0.6066	Remote Similarity	NPD1694	Approved
0.6063	Remote Similarity	NPD6001	Approved
0.6063	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD7900	Approved
0.6063	Remote Similarity	NPD7748	Approved
0.6047	Remote Similarity	NPD6083	Phase 2
0.6047	Remote Similarity	NPD6084	Phase 2
0.6032	Remote Similarity	NPD5694	Approved
0.6	Remote Similarity	NPD6051	Approved
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD6881	Approved
0.6	Remote Similarity	NPD6899	Approved
0.5987	Remote Similarity	NPD6334	Approved
0.5987	Remote Similarity	NPD6333	Approved
0.5986	Remote Similarity	NPD7319	Approved
0.5984	Remote Similarity	NPD4786	Approved
0.597	Remote Similarity	NPD7333	Discontinued
0.5968	Remote Similarity	NPD3573	Approved
0.5956	Remote Similarity	NPD6373	Approved
0.5956	Remote Similarity	NPD6372	Approved
0.5954	Remote Similarity	NPD6404	Discontinued
0.595	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD7751	Phase 1
0.5944	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5942	Remote Similarity	NPD8077	Approved
0.5942	Remote Similarity	NPD8078	Approved
0.5929	Remote Similarity	NPD7754	Approved
0.5929	Remote Similarity	NPD7755	Approved
0.5926	Remote Similarity	NPD5701	Approved
0.5926	Remote Similarity	NPD5697	Approved
0.5923	Remote Similarity	NPD7902	Approved
0.592	Remote Similarity	NPD5208	Approved
0.5912	Remote Similarity	NPD6883	Approved
0.5912	Remote Similarity	NPD7102	Approved
0.5912	Remote Similarity	NPD6420	Discontinued
0.5912	Remote Similarity	NPD7290	Approved
0.5906	Remote Similarity	NPD6079	Approved
0.5906	Remote Similarity	NPD7515	Phase 2
0.5894	Remote Similarity	NPD8415	Approved
0.5887	Remote Similarity	NPD3618	Phase 1
0.5887	Remote Similarity	NPD6098	Approved
0.5882	Remote Similarity	NPD6011	Approved
0.5882	Remote Similarity	NPD6415	Discontinued
0.5878	Remote Similarity	NPD5696	Approved
0.587	Remote Similarity	NPD6847	Approved
0.587	Remote Similarity	NPD6649	Approved
0.587	Remote Similarity	NPD6650	Approved
0.587	Remote Similarity	NPD6617	Approved
0.587	Remote Similarity	NPD6869	Approved
0.587	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.587	Remote Similarity	NPD8130	Phase 1
0.5859	Remote Similarity	NPD4202	Approved
0.5855	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3668	Phase 3
0.5846	Remote Similarity	NPD4697	Phase 3
0.5839	Remote Similarity	NPD8390	Approved
0.5839	Remote Similarity	NPD8391	Approved
0.5839	Remote Similarity	NPD6013	Approved
0.5839	Remote Similarity	NPD6014	Approved
0.5839	Remote Similarity	NPD6012	Approved
0.5839	Remote Similarity	NPD8392	Approved
0.5827	Remote Similarity	NPD6882	Approved
0.5827	Remote Similarity	NPD6053	Discontinued
0.5827	Remote Similarity	NPD8297	Approved
0.5821	Remote Similarity	NPD2259	Approved
0.5821	Remote Similarity	NPD2258	Approved
0.5821	Remote Similarity	NPD6052	Approved
0.582	Remote Similarity	NPD3667	Approved
0.5809	Remote Similarity	NPD6412	Phase 2
0.5802	Remote Similarity	NPD4755	Approved
0.5793	Remote Similarity	NPD7623	Phase 3
0.5793	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD8451	Approved
0.5781	Remote Similarity	NPD5281	Approved
0.5781	Remote Similarity	NPD5284	Approved
0.5769	Remote Similarity	NPD5654	Approved
0.5764	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.5764	Remote Similarity	NPD7147	Phase 3
0.576	Remote Similarity	NPD5279	Phase 3
0.5753	Remote Similarity	NPD7604	Phase 2
0.5753	Remote Similarity	NPD7642	Approved
0.5748	Remote Similarity	NPD4753	Phase 2
0.5746	Remote Similarity	NPD5211	Phase 2
0.5743	Remote Similarity	NPD8448	Approved
0.5735	Remote Similarity	NPD8040	Discontinued
0.5734	Remote Similarity	NPD7327	Approved
0.5734	Remote Similarity	NPD7328	Approved
0.5726	Remote Similarity	NPD3666	Approved
0.5726	Remote Similarity	NPD3665	Phase 1
0.5726	Remote Similarity	NPD3133	Approved
0.5725	Remote Similarity	NPD5221	Approved
0.5725	Remote Similarity	NPD7732	Phase 3
0.5725	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5725	Remote Similarity	NPD5222	Approved
0.5724	Remote Similarity	NPD8033	Approved
0.5723	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6430	Approved
0.5714	Remote Similarity	NPD4700	Approved
0.5714	Remote Similarity	NPD5286	Approved
0.5714	Remote Similarity	NPD4696	Approved
0.5714	Remote Similarity	NPD6429	Approved
0.5714	Remote Similarity	NPD5285	Approved
0.5705	Remote Similarity	NPD2199	Approved
0.5705	Remote Similarity	NPD7736	Approved
0.5705	Remote Similarity	NPD2198	Approved
0.5703	Remote Similarity	NPD4096	Approved
0.5694	Remote Similarity	NPD7516	Approved
0.5691	Remote Similarity	NPD4221	Approved
0.5691	Remote Similarity	NPD4223	Phase 3
0.5687	Remote Similarity	NPD7625	Phase 1
0.5685	Remote Similarity	NPD6370	Approved
0.5682	Remote Similarity	NPD5173	Approved
0.5682	Remote Similarity	NPD5959	Approved
0.568	Remote Similarity	NPD5329	Approved
0.5674	Remote Similarity	NPD1376	Discontinued
0.5672	Remote Similarity	NPD5223	Approved
0.5662	Remote Similarity	NPD5141	Approved
0.5659	Remote Similarity	NPD8034	Phase 2
0.5659	Remote Similarity	NPD8035	Phase 2
0.5655	Remote Similarity	NPD6059	Approved
0.5655	Remote Similarity	NPD8377	Approved
0.5655	Remote Similarity	NPD8294	Approved
0.5655	Remote Similarity	NPD6054	Approved
0.5652	Remote Similarity	NPD6686	Approved
0.5646	Remote Similarity	NPD7830	Approved
0.5646	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.5646	Remote Similarity	NPD7829	Approved
0.5645	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.5643	Remote Similarity	NPD2204	Approved
0.5639	Remote Similarity	NPD4225	Approved
0.5638	Remote Similarity	NPD7747	Phase 1
0.5638	Remote Similarity	NPD7746	Phase 1
0.5638	Remote Similarity	NPD8293	Discontinued
0.5635	Remote Similarity	NPD4694	Approved
0.5635	Remote Similarity	NPD5280	Approved
0.5635	Remote Similarity	NPD5690	Phase 2
0.5635	Remote Similarity	NPD8308	Discontinued
0.563	Remote Similarity	NPD5226	Approved
0.563	Remote Similarity	NPD5225	Approved
0.563	Remote Similarity	NPD5224	Approved
0.563	Remote Similarity	NPD7632	Discontinued
0.563	Remote Similarity	NPD4633	Approved
0.5625	Remote Similarity	NPD7641	Discontinued
0.5625	Remote Similarity	NPD6335	Approved
0.5616	Remote Similarity	NPD8378	Approved
0.5616	Remote Similarity	NPD8380	Approved
0.5616	Remote Similarity	NPD8296	Approved
0.5616	Remote Similarity	NPD8379	Approved
0.5616	Remote Similarity	NPD6921	Approved
0.5616	Remote Similarity	NPD6291	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