NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	544.38
Volume:	581.374
LogP:	4.53
LogD:	3.68
LogS:	-4.73
# Rotatable Bonds:	5
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.343
Synthetic Accessibility Score:	5.188
Fsp3:	0.879
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.078
MDCK Permeability:	2.4309420041390695e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.423
30% Bioavailability (F30%):	0.891

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.75
Plasma Protein Binding (PPB):	72.26131439208984%
Volume Distribution (VD):	0.941
Pgp-substrate:	22.117904663085938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.413
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.043
CYP2C9-substrate:	0.019
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.043
CYP3A4-inhibitor:	0.932
CYP3A4-substrate:	0.699

ADMET: Excretion

Clearance (CL):	5.06
Half-life (T1/2):	0.202

ADMET: Toxicity

hERG Blockers:	0.876
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.532
Carcinogencity:	0.364
Eye Corrosion:	0.007
Eye Irritation:	0.02
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC476879

Natural Product ID:	NPC476879
*Common Name:**	23-Acetoxyimberbic acid 29-methyl ester
IUPAC Name:	methyl (2R,4aS,6aS,6aS,6bR,8aR,9R,10S,12S,12aR,14bS)-9-(acetyloxymethyl)-10,12-dihydroxy-2,4a,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2-carboxylate
Synonyms:	23-Acetoxyimberbic Acid 29-Methyl Ester
Standard InCHIKey:	AXZVVRJAQSRTQU-LHURNMPVSA-N
Standard InCHI:	InChI=1S/C33H52O6/c1-20(34)39-19-30(4)23-11-12-32(6)24(33(23,7)26(36)17-25(30)35)10-9-21-22-18-29(3,27(37)38-8)14-13-28(22,2)15-16-31(21,32)5/h9,22-26,35-36H,10-19H2,1-8H3/t22-,23+,24+,25+,26+,28-,29-,30+,31-,32-,33+/m1/s1
SMILES:	CC(=O)OC[C@]1([C@@H]2CC[C@@]3([C@@H]([C@]2([C@H](C[C@@H]1O)O)C)CC=C4[C@]3(CC[C@@]5([C@@H]4C[C@](CC5)(C)C(=O)OC)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	45267264
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO33642	Combretum sundaicum	Species	Combretaceae	Eukaryota	leaves, flowers	Bac Son, Lang Son Province, Vietnam	1997-JUL	PMID[19572612]
NPO33642	Combretum sundaicum	Species	Combretaceae	Eukaryota	leaves	Bac Son, Lang Son Province, Vietnam	1997-JUL	PMID[19572612]
NPO33642	Combretum sundaicum	Species	Combretaceae	Eukaryota	flowers	Bac Son, Lang Son Province, Vietnam	1997-JUL	PMID[19572612]

☑ 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	3
Ki	1

Activity Type	# Activity
Cell Line	3
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	1700	nM	PMID[19572612]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2900	nM	PMID[19572612]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	4600	nM	PMID[19572612]
NPT2796	Individual Protein	Apoptosis regulator Bcl-X	Homo sapiens	Ki	>	100000	nM	PMID[19572612]

☑ 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 NPC476879 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	226
0.1-0.2	1409
0.2-0.3	4716
0.3-0.4	10352
0.4-0.5	11936
0.5-0.6	5747
0.6-0.7	4883
0.7-0.8	2612
0.8-0.85	355
0.85-0.9	353
0.9-0.95	103
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476878
0.9778	High Similarity	NPC474727
0.9556	High Similarity	NPC86368
0.9451	High Similarity	NPC159365
0.9444	High Similarity	NPC475708
0.9333	High Similarity	NPC120840
0.9333	High Similarity	NPC113989
0.9278	High Similarity	NPC477877
0.9255	High Similarity	NPC260149
0.9255	High Similarity	NPC58942
0.9239	High Similarity	NPC78580
0.9239	High Similarity	NPC184006
0.9239	High Similarity	NPC23621
0.9231	High Similarity	NPC77099
0.9231	High Similarity	NPC285184
0.9231	High Similarity	NPC60755
0.9231	High Similarity	NPC470590
0.9222	High Similarity	NPC225585
0.9222	High Similarity	NPC293048
0.9222	High Similarity	NPC127689
0.9222	High Similarity	NPC30522
0.9222	High Similarity	NPC130520
0.9222	High Similarity	NPC121798
0.9222	High Similarity	NPC263393
0.9222	High Similarity	NPC61543
0.9222	High Similarity	NPC270768
0.9222	High Similarity	NPC59263
0.9222	High Similarity	NPC234346
0.914	High Similarity	NPC23241
0.914	High Similarity	NPC195715
0.9121	High Similarity	NPC470589
0.9121	High Similarity	NPC126369
0.9121	High Similarity	NPC130278
0.9121	High Similarity	NPC474728
0.9121	High Similarity	NPC111110
0.9111	High Similarity	NPC52169
0.9111	High Similarity	NPC40552
0.9111	High Similarity	NPC182797
0.9111	High Similarity	NPC246708
0.9053	High Similarity	NPC475876
0.9053	High Similarity	NPC119036
0.9043	High Similarity	NPC230151
0.9043	High Similarity	NPC307282
0.9043	High Similarity	NPC305464
0.9043	High Similarity	NPC19376
0.9043	High Similarity	NPC327179
0.9043	High Similarity	NPC25848
0.9043	High Similarity	NPC476318
0.9043	High Similarity	NPC476327
0.9032	High Similarity	NPC296164
0.9032	High Similarity	NPC74751
0.9022	High Similarity	NPC324341
0.9022	High Similarity	NPC966
0.9022	High Similarity	NPC228784
0.9022	High Similarity	NPC288833
0.9022	High Similarity	NPC282616
0.9022	High Similarity	NPC155120
0.9011	High Similarity	NPC143232
0.9011	High Similarity	NPC470588
0.9011	High Similarity	NPC64872
0.9011	High Similarity	NPC25906
0.9011	High Similarity	NPC274330
0.9011	High Similarity	NPC290972
0.9011	High Similarity	NPC198664
0.9	High Similarity	NPC171203
0.9	High Similarity	NPC18064
0.9	High Similarity	NPC46912
0.9	High Similarity	NPC130577
0.9	High Similarity	NPC293564
0.9	High Similarity	NPC307426
0.9	High Similarity	NPC142415
0.9	High Similarity	NPC98442
0.9	High Similarity	NPC102683
0.9	High Similarity	NPC242468
0.9	High Similarity	NPC51700
0.9	High Similarity	NPC88716
0.9	High Similarity	NPC310546
0.9	High Similarity	NPC68160
0.9	High Similarity	NPC162107
0.8958	High Similarity	NPC475156
0.8958	High Similarity	NPC473576
0.8947	High Similarity	NPC26413
0.8947	High Similarity	NPC158347
0.8936	High Similarity	NPC473240
0.8925	High Similarity	NPC229281
0.8925	High Similarity	NPC63118
0.8925	High Similarity	NPC295643
0.8925	High Similarity	NPC136313
0.8925	High Similarity	NPC272075
0.8925	High Similarity	NPC474436
0.8925	High Similarity	NPC307335
0.8925	High Similarity	NPC74855
0.8925	High Similarity	NPC214756
0.8925	High Similarity	NPC49776
0.8913	High Similarity	NPC291028
0.8913	High Similarity	NPC120968
0.8913	High Similarity	NPC210037
0.8913	High Similarity	NPC477872
0.8913	High Similarity	NPC290614
0.8913	High Similarity	NPC227467
0.8913	High Similarity	NPC7260
0.8913	High Similarity	NPC86372
0.8913	High Similarity	NPC273621
0.8913	High Similarity	NPC172361
0.8913	High Similarity	NPC18872
0.8911	High Similarity	NPC476881
0.8911	High Similarity	NPC476883
0.8911	High Similarity	NPC476885
0.8911	High Similarity	NPC476882
0.8911	High Similarity	NPC476886
0.8911	High Similarity	NPC476884
0.8911	High Similarity	NPC476880
0.8911	High Similarity	NPC476887
0.8901	High Similarity	NPC290690
0.8901	High Similarity	NPC17733
0.8901	High Similarity	NPC474512
0.8901	High Similarity	NPC181225
0.8901	High Similarity	NPC473242
0.8901	High Similarity	NPC470629
0.8889	High Similarity	NPC325594
0.8889	High Similarity	NPC91525
0.8889	High Similarity	NPC10005
0.8889	High Similarity	NPC329943
0.8889	High Similarity	NPC72638
0.8889	High Similarity	NPC9892
0.8866	High Similarity	NPC118964
0.8866	High Similarity	NPC476132
0.8866	High Similarity	NPC256247
0.8854	High Similarity	NPC471966
0.8854	High Similarity	NPC164349
0.8854	High Similarity	NPC477875
0.8854	High Similarity	NPC477876
0.8842	High Similarity	NPC98874
0.883	High Similarity	NPC263548
0.883	High Similarity	NPC282395
0.883	High Similarity	NPC299996
0.883	High Similarity	NPC20235
0.883	High Similarity	NPC145667
0.883	High Similarity	NPC6818
0.883	High Similarity	NPC474963
0.883	High Similarity	NPC231063
0.883	High Similarity	NPC222047
0.883	High Similarity	NPC91010
0.883	High Similarity	NPC191412
0.883	High Similarity	NPC32407
0.883	High Similarity	NPC114159
0.883	High Similarity	NPC88116
0.8817	High Similarity	NPC71074
0.8817	High Similarity	NPC105189
0.8817	High Similarity	NPC187722
0.8817	High Similarity	NPC25299
0.8817	High Similarity	NPC6255
0.8817	High Similarity	NPC84319
0.8817	High Similarity	NPC306541
0.8817	High Similarity	NPC472149
0.8817	High Similarity	NPC4036
0.8817	High Similarity	NPC233455
0.8817	High Similarity	NPC474525
0.8817	High Similarity	NPC300351
0.8817	High Similarity	NPC145067
0.8817	High Similarity	NPC52021
0.8817	High Similarity	NPC65120
0.8817	High Similarity	NPC158030
0.8817	High Similarity	NPC235884
0.8817	High Similarity	NPC471588
0.8812	High Similarity	NPC204407
0.8812	High Similarity	NPC237503
0.8812	High Similarity	NPC57362
0.8812	High Similarity	NPC167383
0.8812	High Similarity	NPC306746
0.8804	High Similarity	NPC475049
0.8804	High Similarity	NPC474972
0.8804	High Similarity	NPC161751
0.8804	High Similarity	NPC95246
0.88	High Similarity	NPC473538
0.88	High Similarity	NPC283849
0.8778	High Similarity	NPC191965
0.8763	High Similarity	NPC254567
0.8763	High Similarity	NPC476195
0.8763	High Similarity	NPC474571
0.875	High Similarity	NPC43686
0.875	High Similarity	NPC189880
0.8737	High Similarity	NPC148523
0.8737	High Similarity	NPC279974
0.8725	High Similarity	NPC7870
0.8725	High Similarity	NPC29069
0.8725	High Similarity	NPC199457
0.8725	High Similarity	NPC127056
0.8725	High Similarity	NPC108709
0.8725	High Similarity	NPC56713
0.8725	High Similarity	NPC475296
0.8725	High Similarity	NPC174679
0.8725	High Similarity	NPC75747
0.8725	High Similarity	NPC279554
0.8725	High Similarity	NPC59804
0.8725	High Similarity	NPC270667
0.8725	High Similarity	NPC274507
0.8725	High Similarity	NPC136877
0.8725	High Similarity	NPC68419
0.8725	High Similarity	NPC474589

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 NPC476879 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1727
0.2-0.3	3801
0.3-0.4	2234
0.4-0.5	713
0.5-0.6	237
0.6-0.7	188
0.7-0.8	49
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9032	High Similarity	NPD7748	Approved
0.8817	High Similarity	NPD7515	Phase 2
0.875	High Similarity	NPD7902	Approved
0.8438	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7900	Approved
0.8111	Intermediate Similarity	NPD7645	Phase 2
0.81	Intermediate Similarity	NPD7638	Approved
0.8041	Intermediate Similarity	NPD8035	Phase 2
0.8041	Intermediate Similarity	NPD8034	Phase 2
0.802	Intermediate Similarity	NPD7639	Approved
0.802	Intermediate Similarity	NPD7640	Approved
0.7979	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD8328	Phase 3
0.7778	Intermediate Similarity	NPD6399	Phase 3
0.7748	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6675	Approved
0.7642	Intermediate Similarity	NPD5739	Approved
0.7642	Intermediate Similarity	NPD6402	Approved
0.7642	Intermediate Similarity	NPD7128	Approved
0.7551	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD6411	Approved
0.75	Intermediate Similarity	NPD6899	Approved
0.75	Intermediate Similarity	NPD4786	Approved
0.7476	Intermediate Similarity	NPD6084	Phase 2
0.7476	Intermediate Similarity	NPD6083	Phase 2
0.7475	Intermediate Similarity	NPD5328	Approved
0.7474	Intermediate Similarity	NPD3667	Approved
0.7455	Intermediate Similarity	NPD8130	Phase 1
0.7431	Intermediate Similarity	NPD6373	Approved
0.7431	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6372	Approved
0.7407	Intermediate Similarity	NPD5701	Approved
0.7407	Intermediate Similarity	NPD5697	Approved
0.7407	Intermediate Similarity	NPD6412	Phase 2
0.7387	Intermediate Similarity	NPD8297	Approved
0.7364	Intermediate Similarity	NPD7102	Approved
0.7364	Intermediate Similarity	NPD7290	Approved
0.7364	Intermediate Similarity	NPD6883	Approved
0.7358	Intermediate Similarity	NPD7632	Discontinued
0.7347	Intermediate Similarity	NPD5330	Approved
0.7347	Intermediate Similarity	NPD7146	Approved
0.7347	Intermediate Similarity	NPD7521	Approved
0.7347	Intermediate Similarity	NPD7334	Approved
0.7347	Intermediate Similarity	NPD6684	Approved
0.7347	Intermediate Similarity	NPD6409	Approved
0.7327	Intermediate Similarity	NPD6079	Approved
0.7321	Intermediate Similarity	NPD8133	Approved
0.73	Intermediate Similarity	NPD6101	Approved
0.73	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6649	Approved
0.7297	Intermediate Similarity	NPD6847	Approved
0.7297	Intermediate Similarity	NPD6617	Approved
0.7297	Intermediate Similarity	NPD6650	Approved
0.7297	Intermediate Similarity	NPD6869	Approved
0.7273	Intermediate Similarity	NPD3573	Approved
0.7273	Intermediate Similarity	NPD6014	Approved
0.7273	Intermediate Similarity	NPD6012	Approved
0.7273	Intermediate Similarity	NPD6013	Approved
0.7255	Intermediate Similarity	NPD5779	Approved
0.7255	Intermediate Similarity	NPD5778	Approved
0.725	Intermediate Similarity	NPD7736	Approved
0.7234	Intermediate Similarity	NPD6114	Approved
0.7234	Intermediate Similarity	NPD6697	Approved
0.7234	Intermediate Similarity	NPD6118	Approved
0.7234	Intermediate Similarity	NPD6115	Approved
0.7232	Intermediate Similarity	NPD6882	Approved
0.7207	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6903	Approved
0.72	Intermediate Similarity	NPD6672	Approved
0.72	Intermediate Similarity	NPD5737	Approved
0.7182	Intermediate Similarity	NPD6686	Approved
0.7182	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD6011	Approved
0.7168	Intermediate Similarity	NPD4632	Approved
0.7156	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD3665	Phase 1
0.7143	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD3133	Approved
0.7143	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3666	Approved
0.713	Intermediate Similarity	NPD7115	Discovery
0.7115	Intermediate Similarity	NPD5695	Phase 3
0.7094	Intermediate Similarity	NPD6319	Approved
0.7087	Intermediate Similarity	NPD4202	Approved
0.7083	Intermediate Similarity	NPD7525	Registered
0.7083	Intermediate Similarity	NPD7507	Approved
0.7075	Intermediate Similarity	NPD5696	Approved
0.7049	Intermediate Similarity	NPD7319	Approved
0.7048	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5222	Approved
0.7048	Intermediate Similarity	NPD5221	Approved
0.7048	Intermediate Similarity	NPD4697	Phase 3
0.7034	Intermediate Similarity	NPD8379	Approved
0.7034	Intermediate Similarity	NPD8296	Approved
0.7034	Intermediate Similarity	NPD8378	Approved
0.7034	Intermediate Similarity	NPD8380	Approved
0.7034	Intermediate Similarity	NPD8335	Approved
0.7025	Intermediate Similarity	NPD8293	Discontinued
0.7021	Intermediate Similarity	NPD6117	Approved
0.7009	Intermediate Similarity	NPD5286	Approved
0.7009	Intermediate Similarity	NPD4700	Approved
0.7009	Intermediate Similarity	NPD4696	Approved
0.7009	Intermediate Similarity	NPD5285	Approved
0.7	Intermediate Similarity	NPD7492	Approved
0.699	Remote Similarity	NPD7637	Suspended
0.6983	Remote Similarity	NPD6009	Approved
0.6981	Remote Similarity	NPD5173	Approved
0.697	Remote Similarity	NPD3668	Phase 3
0.6961	Remote Similarity	NPD4753	Phase 2
0.6952	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8294	Approved
0.6949	Remote Similarity	NPD6054	Approved
0.6949	Remote Similarity	NPD6059	Approved
0.6949	Remote Similarity	NPD8377	Approved
0.6947	Remote Similarity	NPD6116	Phase 1
0.6942	Remote Similarity	NPD6616	Approved
0.6937	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7327	Approved
0.6923	Remote Similarity	NPD7328	Approved
0.6917	Remote Similarity	NPD7604	Phase 2
0.6916	Remote Similarity	NPD4225	Approved
0.6897	Remote Similarity	NPD6274	Approved
0.6897	Remote Similarity	NPD6868	Approved
0.6891	Remote Similarity	NPD5983	Phase 2
0.6891	Remote Similarity	NPD8033	Approved
0.6887	Remote Similarity	NPD7732	Phase 3
0.6887	Remote Similarity	NPD7614	Phase 1
0.6885	Remote Similarity	NPD7078	Approved
0.6881	Remote Similarity	NPD5211	Phase 2
0.6881	Remote Similarity	NPD5225	Approved
0.6881	Remote Similarity	NPD5226	Approved
0.6881	Remote Similarity	NPD5224	Approved
0.6881	Remote Similarity	NPD4633	Approved
0.6864	Remote Similarity	NPD7516	Approved
0.6864	Remote Similarity	NPD7100	Approved
0.6864	Remote Similarity	NPD7101	Approved
0.6833	Remote Similarity	NPD6370	Approved
0.6832	Remote Similarity	NPD6098	Approved
0.6818	Remote Similarity	NPD5175	Approved
0.6818	Remote Similarity	NPD5174	Approved
0.6809	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD6336	Discontinued
0.6796	Remote Similarity	NPD6080	Approved
0.6796	Remote Similarity	NPD6673	Approved
0.6796	Remote Similarity	NPD6904	Approved
0.6789	Remote Similarity	NPD5223	Approved
0.678	Remote Similarity	NPD6335	Approved
0.6768	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5141	Approved
0.6754	Remote Similarity	NPD4634	Approved
0.675	Remote Similarity	NPD6015	Approved
0.675	Remote Similarity	NPD6909	Approved
0.675	Remote Similarity	NPD6016	Approved
0.675	Remote Similarity	NPD6908	Approved
0.6737	Remote Similarity	NPD6942	Approved
0.6737	Remote Similarity	NPD7339	Approved
0.6735	Remote Similarity	NPD4695	Discontinued
0.67	Remote Similarity	NPD6695	Phase 3
0.6696	Remote Similarity	NPD4767	Approved
0.6696	Remote Similarity	NPD4768	Approved
0.6695	Remote Similarity	NPD6317	Approved
0.6694	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6314	Approved
0.6639	Remote Similarity	NPD6067	Discontinued
0.6639	Remote Similarity	NPD6313	Approved
0.6638	Remote Similarity	NPD6053	Discontinued
0.6636	Remote Similarity	NPD5210	Approved
0.6636	Remote Similarity	NPD4629	Approved
0.6634	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8517	Approved
0.6612	Remote Similarity	NPD8516	Approved
0.6612	Remote Similarity	NPD8515	Approved
0.6612	Remote Similarity	NPD8513	Phase 3
0.6612	Remote Similarity	NPD7503	Approved
0.6602	Remote Similarity	NPD7750	Discontinued
0.66	Remote Similarity	NPD4221	Approved
0.66	Remote Similarity	NPD4223	Phase 3
0.6579	Remote Similarity	NPD5128	Approved
0.6579	Remote Similarity	NPD4730	Approved
0.6579	Remote Similarity	NPD4729	Approved
0.6571	Remote Similarity	NPD46	Approved
0.6571	Remote Similarity	NPD6698	Approved
0.6569	Remote Similarity	NPD1694	Approved
0.6569	Remote Similarity	NPD5329	Approved
0.6562	Remote Similarity	NPD3703	Phase 2
0.6542	Remote Similarity	NPD6001	Approved
0.6538	Remote Similarity	NPD5208	Approved
0.6535	Remote Similarity	NPD4788	Approved
0.6509	Remote Similarity	NPD5284	Approved
0.6509	Remote Similarity	NPD5281	Approved
0.6509	Remote Similarity	NPD6050	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