NPASS Compound

Structure

NPC281880 OpenBabel07101718302D 23 24 0 0 1 0 0 0 0 0999 V2000 3.4641 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -6.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 2 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 8 1 0 0 0 0 6 13 1 0 0 0 0 7 9 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 16 1 0 0 0 0 10 11 1 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 18 1 0 0 0 0 14 15 1 0 0 0 0 15 20 1 1 0 0 0 16 19 1 0 0 0 0 16 20 1 1 0 0 0 17 19 1 0 0 0 0 17 21 1 6 0 0 0 18 22 2 0 0 0 0 18 23 1 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	355.825
LogP:	4.451
LogD:	3.25
LogS:	-3.403
# Rotatable Bonds:	4
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.746
Synthetic Accessibility Score:	4.174
Fsp3:	0.75
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:	-5.013
MDCK Permeability:	1.2400470041029621e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.942
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.326
Plasma Protein Binding (PPB):	85.93968200683594%
Volume Distribution (VD):	0.268
Pgp-substrate:	12.69991397857666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.082
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.532
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.855
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.34
CYP3A4-inhibitor:	0.022
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	12.167
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.18
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.519
Carcinogencity:	0.502
Eye Corrosion:	0.836
Eye Irritation:	0.577
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC281880

Natural Product ID:	NPC281880
*Common Name:**	3Beta-Hydroxycopalic Acid
IUPAC Name:	(E)-5-[(1R,4aS,6S,8aS)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-enoic acid
Synonyms:	3Beta-Hydroxycopalic Acid
Standard InCHIKey:	LNWOKEZJIRLIDO-FCFWMCEOSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-13(12-18(22)23)6-8-15-14(2)7-9-16-19(3,4)17(21)10-11-20(15,16)5/h12,15-17,21H,2,6-11H2,1,3-5H3,(H,22,23)/b13-12+/t15-,16-,17+,20+/m1/s1
SMILES:	C/C(=CC(=O)O)/CC[C@@H]1C(=C)CC[C@@H]2C(C)(C)[C@H](CC[C@@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2048914
PubChem CID:	70692610
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO32774	Copaifera	Genus	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22440015]

☑ 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
EC50	1
IC50	2
Others	12

Activity Type	# Activity
Cell Line	1
Organism	12
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2679	Cell Line	LLC-MK2	Macaca mulatta	CC50	=	31200.0	nM	PMID[492521]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	41200.0	nM	PMID[492521]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	EC50	=	453100.0	nM	PMID[492521]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	1800.0	nM	PMID[492521]
NPT27	Others	Unspecified		HC50	=	125.0	uM	PMID[492521]
NPT27	Others	Unspecified		Ratio CC50/IC50	=	17.3	n.a.	PMID[492521]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	40.0	%	PMID[492521]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	2.56	%	PMID[492521]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	0.15	%	PMID[492521]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	24.29	%	PMID[492521]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	73.0	%	PMID[492521]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	2.27	%	PMID[492521]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	0.01	%	PMID[492521]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	73.66	%	PMID[492521]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	Activity	=	24.06	%	PMID[492521]

☑ 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 NPC281880 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	171
0.1-0.2	1109
0.2-0.3	4658
0.3-0.4	13251
0.4-0.5	10282
0.5-0.6	6705
0.6-0.7	4468
0.7-0.8	1808
0.8-0.85	172
0.85-0.9	56
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9867	High Similarity	NPC159148
0.9481	High Similarity	NPC2524
0.9359	High Similarity	NPC79945
0.9351	High Similarity	NPC170303
0.925	High Similarity	NPC475069
0.925	High Similarity	NPC175145
0.9125	High Similarity	NPC109528
0.9114	High Similarity	NPC476927
0.9079	High Similarity	NPC132542
0.9024	High Similarity	NPC104560
0.9	High Similarity	NPC306951
0.8987	High Similarity	NPC256112
0.8916	High Similarity	NPC262858
0.8916	High Similarity	NPC472240
0.881	High Similarity	NPC78973
0.878	High Similarity	NPC131813
0.8765	High Similarity	NPC102048
0.8706	High Similarity	NPC74296
0.8706	High Similarity	NPC110923
0.869	High Similarity	NPC314727
0.869	High Similarity	NPC146554
0.8684	High Similarity	NPC201048
0.8684	High Similarity	NPC306727
0.8684	High Similarity	NPC476366
0.8642	High Similarity	NPC311070
0.8642	High Similarity	NPC57370
0.8625	High Similarity	NPC142163
0.8605	High Similarity	NPC476304
0.8605	High Similarity	NPC53555
0.859	High Similarity	NPC470758
0.859	High Similarity	NPC470711
0.859	High Similarity	NPC470428
0.8571	High Similarity	NPC291665
0.8537	High Similarity	NPC302360
0.8506	High Similarity	NPC119562
0.8506	High Similarity	NPC279410
0.8506	High Similarity	NPC476186
0.8488	Intermediate Similarity	NPC329842
0.8488	Intermediate Similarity	NPC472811
0.8488	Intermediate Similarity	NPC212948
0.8481	Intermediate Similarity	NPC476949
0.8481	Intermediate Similarity	NPC239098
0.8471	Intermediate Similarity	NPC50488
0.8471	Intermediate Similarity	NPC474396
0.8462	Intermediate Similarity	NPC470749
0.8452	Intermediate Similarity	NPC166857
0.8421	Intermediate Similarity	NPC167706
0.8391	Intermediate Similarity	NPC214697
0.8391	Intermediate Similarity	NPC472812
0.8391	Intermediate Similarity	NPC38232
0.8378	Intermediate Similarity	NPC68703
0.8378	Intermediate Similarity	NPC69649
0.8375	Intermediate Similarity	NPC242767
0.8375	Intermediate Similarity	NPC470429
0.8375	Intermediate Similarity	NPC100906
0.8372	Intermediate Similarity	NPC310479
0.8372	Intermediate Similarity	NPC221111
0.8372	Intermediate Similarity	NPC280149
0.8372	Intermediate Similarity	NPC182136
0.8354	Intermediate Similarity	NPC91594
0.8354	Intermediate Similarity	NPC283619
0.8353	Intermediate Similarity	NPC7280
0.8353	Intermediate Similarity	NPC229612
0.8333	Intermediate Similarity	NPC82979
0.8333	Intermediate Similarity	NPC473226
0.8333	Intermediate Similarity	NPC329692
0.8333	Intermediate Similarity	NPC472985
0.8333	Intermediate Similarity	NPC472986
0.8333	Intermediate Similarity	NPC32832
0.8315	Intermediate Similarity	NPC301534
0.8315	Intermediate Similarity	NPC195366
0.8315	Intermediate Similarity	NPC250757
0.8315	Intermediate Similarity	NPC114743
0.8313	Intermediate Similarity	NPC96055
0.8295	Intermediate Similarity	NPC57117
0.8295	Intermediate Similarity	NPC105490
0.8289	Intermediate Similarity	NPC34834
0.8276	Intermediate Similarity	NPC72845
0.8272	Intermediate Similarity	NPC295131
0.8272	Intermediate Similarity	NPC96362
0.8256	Intermediate Similarity	NPC16265
0.8256	Intermediate Similarity	NPC170633
0.8256	Intermediate Similarity	NPC472973
0.825	Intermediate Similarity	NPC476314
0.825	Intermediate Similarity	NPC11908
0.8228	Intermediate Similarity	NPC253190
0.8228	Intermediate Similarity	NPC265588
0.8222	Intermediate Similarity	NPC99726
0.8222	Intermediate Similarity	NPC253826
0.8214	Intermediate Similarity	NPC191965
0.8214	Intermediate Similarity	NPC35933
0.8214	Intermediate Similarity	NPC474013
0.8205	Intermediate Similarity	NPC477138
0.8205	Intermediate Similarity	NPC243342
0.8205	Intermediate Similarity	NPC91858
0.8205	Intermediate Similarity	NPC78527
0.8202	Intermediate Similarity	NPC472441
0.8202	Intermediate Similarity	NPC276110
0.8193	Intermediate Similarity	NPC42476
0.8193	Intermediate Similarity	NPC52108
0.8193	Intermediate Similarity	NPC474789
0.8182	Intermediate Similarity	NPC477792
0.8182	Intermediate Similarity	NPC152778
0.8182	Intermediate Similarity	NPC139692
0.8182	Intermediate Similarity	NPC162615
0.8182	Intermediate Similarity	NPC7349
0.8182	Intermediate Similarity	NPC205034
0.8171	Intermediate Similarity	NPC476646
0.8171	Intermediate Similarity	NPC473420
0.8171	Intermediate Similarity	NPC249423
0.8161	Intermediate Similarity	NPC232202
0.8158	Intermediate Similarity	NPC9942
0.8148	Intermediate Similarity	NPC308038
0.8148	Intermediate Similarity	NPC30986
0.8148	Intermediate Similarity	NPC209430
0.814	Intermediate Similarity	NPC472810
0.814	Intermediate Similarity	NPC472809
0.8132	Intermediate Similarity	NPC478056
0.8132	Intermediate Similarity	NPC218107
0.8132	Intermediate Similarity	NPC325229
0.8132	Intermediate Similarity	NPC275086
0.8125	Intermediate Similarity	NPC203403
0.8125	Intermediate Similarity	NPC61952
0.8125	Intermediate Similarity	NPC149550
0.8125	Intermediate Similarity	NPC85105
0.8118	Intermediate Similarity	NPC322159
0.8118	Intermediate Similarity	NPC84121
0.8118	Intermediate Similarity	NPC73038
0.8118	Intermediate Similarity	NPC137306
0.8118	Intermediate Similarity	NPC325594
0.8118	Intermediate Similarity	NPC474970
0.8111	Intermediate Similarity	NPC234993
0.8111	Intermediate Similarity	NPC134072
0.8111	Intermediate Similarity	NPC190713
0.8111	Intermediate Similarity	NPC473153
0.8111	Intermediate Similarity	NPC16967
0.8111	Intermediate Similarity	NPC242848
0.8108	Intermediate Similarity	NPC107258
0.8101	Intermediate Similarity	NPC291503
0.8101	Intermediate Similarity	NPC477923
0.8101	Intermediate Similarity	NPC66566
0.809	Intermediate Similarity	NPC191521
0.809	Intermediate Similarity	NPC470255
0.8077	Intermediate Similarity	NPC68443
0.8077	Intermediate Similarity	NPC182717
0.8072	Intermediate Similarity	NPC155521
0.8072	Intermediate Similarity	NPC296701
0.8072	Intermediate Similarity	NPC224455
0.8072	Intermediate Similarity	NPC93590
0.8072	Intermediate Similarity	NPC218616
0.8068	Intermediate Similarity	NPC472978
0.8068	Intermediate Similarity	NPC233455
0.8068	Intermediate Similarity	NPC145067
0.8068	Intermediate Similarity	NPC158030
0.8068	Intermediate Similarity	NPC65120
0.8068	Intermediate Similarity	NPC4036
0.8049	Intermediate Similarity	NPC469802
0.8046	Intermediate Similarity	NPC472983
0.8046	Intermediate Similarity	NPC246028
0.8046	Intermediate Similarity	NPC473999
0.8046	Intermediate Similarity	NPC82876
0.8046	Intermediate Similarity	NPC309603
0.8043	Intermediate Similarity	NPC251680
0.8043	Intermediate Similarity	NPC38855
0.8043	Intermediate Similarity	NPC470074
0.8043	Intermediate Similarity	NPC324841
0.8043	Intermediate Similarity	NPC266955
0.8026	Intermediate Similarity	NPC471238
0.8026	Intermediate Similarity	NPC96484
0.8025	Intermediate Similarity	NPC167891
0.8025	Intermediate Similarity	NPC83351
0.8025	Intermediate Similarity	NPC198240
0.8023	Intermediate Similarity	NPC142415
0.8023	Intermediate Similarity	NPC130577
0.8023	Intermediate Similarity	NPC293564
0.8023	Intermediate Similarity	NPC473891
0.8023	Intermediate Similarity	NPC142361
0.8023	Intermediate Similarity	NPC68160
0.8023	Intermediate Similarity	NPC51700
0.8023	Intermediate Similarity	NPC242468
0.8023	Intermediate Similarity	NPC171203
0.8023	Intermediate Similarity	NPC474684
0.8023	Intermediate Similarity	NPC307426
0.8023	Intermediate Similarity	NPC18064
0.8023	Intermediate Similarity	NPC88716
0.8023	Intermediate Similarity	NPC245004
0.8023	Intermediate Similarity	NPC98442
0.8023	Intermediate Similarity	NPC102683
0.8022	Intermediate Similarity	NPC141401
0.8022	Intermediate Similarity	NPC73911
0.8022	Intermediate Similarity	NPC51499
0.8	Intermediate Similarity	NPC476602
0.8	Intermediate Similarity	NPC167873
0.8	Intermediate Similarity	NPC53565
0.8	Intermediate Similarity	NPC1973
0.8	Intermediate Similarity	NPC266899
0.8	Intermediate Similarity	NPC52628
0.8	Intermediate Similarity	NPC164424
0.8	Intermediate Similarity	NPC470574
0.7978	Intermediate Similarity	NPC214756

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 NPC281880 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1420
0.2-0.3	3926
0.3-0.4	2459
0.4-0.5	737
0.5-0.6	202
0.6-0.7	218
0.7-0.8	34
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
0.8068	Intermediate Similarity	NPD7515	Phase 2
0.8043	Intermediate Similarity	NPD7640	Approved
0.8043	Intermediate Similarity	NPD7639	Approved
0.7935	Intermediate Similarity	NPD7638	Approved
0.7935	Intermediate Similarity	NPD4225	Approved
0.7711	Intermediate Similarity	NPD7645	Phase 2
0.7701	Intermediate Similarity	NPD3618	Phase 1
0.7692	Intermediate Similarity	NPD7748	Approved
0.7654	Intermediate Similarity	NPD8264	Approved
0.764	Intermediate Similarity	NPD5328	Approved
0.7619	Intermediate Similarity	NPD7525	Registered
0.7473	Intermediate Similarity	NPD6079	Approved
0.7447	Intermediate Similarity	NPD7902	Approved
0.7439	Intermediate Similarity	NPD6942	Approved
0.7439	Intermediate Similarity	NPD7339	Approved
0.7386	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7632	Discontinued
0.7317	Intermediate Similarity	NPD6924	Approved
0.7317	Intermediate Similarity	NPD6926	Approved
0.7294	Intermediate Similarity	NPD6929	Approved
0.7273	Intermediate Similarity	NPD3666	Approved
0.7273	Intermediate Similarity	NPD3133	Approved
0.7273	Intermediate Similarity	NPD4786	Approved
0.7273	Intermediate Similarity	NPD3665	Phase 1
0.7241	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3667	Approved
0.7209	Intermediate Similarity	NPD6931	Approved
0.7209	Intermediate Similarity	NPD6930	Phase 2
0.7204	Intermediate Similarity	NPD4202	Approved
0.7176	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6933	Approved
0.7128	Intermediate Similarity	NPD7900	Approved
0.7128	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7146	Approved
0.7111	Intermediate Similarity	NPD6684	Approved
0.7111	Intermediate Similarity	NPD7521	Approved
0.7111	Intermediate Similarity	NPD7334	Approved
0.7111	Intermediate Similarity	NPD6409	Approved
0.7111	Intermediate Similarity	NPD5330	Approved
0.71	Intermediate Similarity	NPD5739	Approved
0.71	Intermediate Similarity	NPD7128	Approved
0.71	Intermediate Similarity	NPD6675	Approved
0.71	Intermediate Similarity	NPD6402	Approved
0.7097	Intermediate Similarity	NPD7637	Suspended
0.7079	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7151	Approved
0.7073	Intermediate Similarity	NPD7152	Approved
0.7073	Intermediate Similarity	NPD7150	Approved
0.7059	Intermediate Similarity	NPD6925	Approved
0.7059	Intermediate Similarity	NPD5776	Phase 2
0.7041	Intermediate Similarity	NPD5344	Discontinued
0.7037	Intermediate Similarity	NPD6923	Approved
0.7037	Intermediate Similarity	NPD6922	Approved
0.7033	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD6399	Phase 3
0.7011	Intermediate Similarity	NPD7509	Discontinued
0.7011	Intermediate Similarity	NPD7332	Phase 2
0.7011	Intermediate Similarity	NPD7514	Phase 3
0.6979	Remote Similarity	NPD5221	Approved
0.6979	Remote Similarity	NPD5222	Approved
0.6979	Remote Similarity	NPD4697	Phase 3
0.6979	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7145	Approved
0.6977	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5211	Phase 2
0.6966	Remote Similarity	NPD6695	Phase 3
0.6961	Remote Similarity	NPD6881	Approved
0.6961	Remote Similarity	NPD7320	Approved
0.6961	Remote Similarity	NPD6899	Approved
0.6957	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6903	Approved
0.6951	Remote Similarity	NPD7144	Approved
0.6951	Remote Similarity	NPD7143	Approved
0.6932	Remote Similarity	NPD6902	Approved
0.6923	Remote Similarity	NPD5279	Phase 3
0.6923	Remote Similarity	NPD4623	Approved
0.6923	Remote Similarity	NPD4519	Discontinued
0.6916	Remote Similarity	NPD7115	Discovery
0.6907	Remote Similarity	NPD5173	Approved
0.6907	Remote Similarity	NPD6083	Phase 2
0.6907	Remote Similarity	NPD6084	Phase 2
0.6907	Remote Similarity	NPD4755	Approved
0.6897	Remote Similarity	NPD4195	Approved
0.6893	Remote Similarity	NPD6373	Approved
0.6893	Remote Similarity	NPD6372	Approved
0.6889	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6051	Approved
0.6863	Remote Similarity	NPD5701	Approved
0.6863	Remote Similarity	NPD5697	Approved
0.6848	Remote Similarity	NPD3573	Approved
0.6842	Remote Similarity	NPD5779	Approved
0.6842	Remote Similarity	NPD5778	Approved
0.6837	Remote Similarity	NPD5290	Discontinued
0.6832	Remote Similarity	NPD5141	Approved
0.6827	Remote Similarity	NPD7290	Approved
0.6827	Remote Similarity	NPD6883	Approved
0.6827	Remote Similarity	NPD7102	Approved
0.6818	Remote Similarity	NPD4695	Discontinued
0.6813	Remote Similarity	NPD6893	Approved
0.6813	Remote Similarity	NPD1694	Approved
0.6796	Remote Similarity	NPD6686	Approved
0.6796	Remote Similarity	NPD6011	Approved
0.6795	Remote Similarity	NPD368	Approved
0.6795	Remote Similarity	NPD4193	Approved
0.6795	Remote Similarity	NPD4191	Approved
0.6795	Remote Similarity	NPD4194	Approved
0.6795	Remote Similarity	NPD4192	Approved
0.6774	Remote Similarity	NPD6672	Approved
0.6774	Remote Similarity	NPD5737	Approved
0.6768	Remote Similarity	NPD4700	Approved
0.6768	Remote Similarity	NPD5286	Approved
0.6768	Remote Similarity	NPD5285	Approved
0.6768	Remote Similarity	NPD6648	Approved
0.6768	Remote Similarity	NPD4696	Approved
0.6762	Remote Similarity	NPD6869	Approved
0.6762	Remote Similarity	NPD6649	Approved
0.6762	Remote Similarity	NPD8130	Phase 1
0.6762	Remote Similarity	NPD6650	Approved
0.6762	Remote Similarity	NPD6617	Approved
0.6762	Remote Similarity	NPD6847	Approved
0.6762	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6898	Phase 1
0.6737	Remote Similarity	NPD6411	Approved
0.6737	Remote Similarity	NPD8035	Phase 2
0.6737	Remote Similarity	NPD8034	Phase 2
0.6731	Remote Similarity	NPD6014	Approved
0.6731	Remote Similarity	NPD6013	Approved
0.6731	Remote Similarity	NPD6012	Approved
0.6702	Remote Similarity	NPD4753	Phase 2
0.6702	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5223	Approved
0.6698	Remote Similarity	NPD6882	Approved
0.6698	Remote Similarity	NPD8297	Approved
0.6697	Remote Similarity	NPD7327	Approved
0.6697	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD6932	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6636	Remote Similarity	NPD7516	Approved
0.6634	Remote Similarity	NPD4633	Approved
0.6634	Remote Similarity	NPD5224	Approved
0.6634	Remote Similarity	NPD5226	Approved
0.6634	Remote Similarity	NPD5225	Approved
0.6632	Remote Similarity	NPD5785	Approved
0.663	Remote Similarity	NPD1696	Phase 3
0.663	Remote Similarity	NPD5363	Approved
0.663	Remote Similarity	NPD5329	Approved
0.6629	Remote Similarity	NPD4820	Approved
0.6629	Remote Similarity	NPD4822	Approved
0.6629	Remote Similarity	NPD4821	Approved
0.6629	Remote Similarity	NPD4819	Approved
0.6629	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5332	Approved
0.6593	Remote Similarity	NPD5331	Approved
0.6593	Remote Similarity	NPD5362	Discontinued
0.6591	Remote Similarity	NPD4271	Approved
0.6591	Remote Similarity	NPD4268	Approved
0.6577	Remote Similarity	NPD8294	Approved
0.6577	Remote Similarity	NPD8377	Approved
0.6571	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5174	Approved
0.6569	Remote Similarity	NPD5175	Approved
0.6569	Remote Similarity	NPD4754	Approved
0.6559	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4790	Discontinued
0.6552	Remote Similarity	NPD6117	Approved
0.6543	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD5695	Phase 3
0.6531	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6101	Approved
0.6522	Remote Similarity	NPD3668	Phase 3
0.6522	Remote Similarity	NPD4197	Approved
0.6518	Remote Similarity	NPD8380	Approved
0.6518	Remote Similarity	NPD8335	Approved
0.6518	Remote Similarity	NPD8033	Approved
0.6518	Remote Similarity	NPD8379	Approved
0.6518	Remote Similarity	NPD8378	Approved
0.6518	Remote Similarity	NPD8296	Approved
0.6517	Remote Similarity	NPD6683	Phase 2
0.6514	Remote Similarity	NPD6868	Approved
0.6512	Remote Similarity	NPD4784	Approved
0.6512	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4785	Approved
0.65	Remote Similarity	NPD5696	Approved
0.6484	Remote Similarity	NPD4270	Approved
0.6484	Remote Similarity	NPD4269	Approved
0.6481	Remote Similarity	NPD4632	Approved
0.6477	Remote Similarity	NPD6116	Phase 1
0.6447	Remote Similarity	NPD342	Phase 1
0.6444	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4748	Discontinued
0.6442	Remote Similarity	NPD4768	Approved
0.6442	Remote Similarity	NPD4767	Approved
0.6436	Remote Similarity	NPD6404	Discontinued
0.6413	Remote Similarity	NPD4788	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