NPASS Compound

Structure

NPC475069 OpenBabel07101718312D 24 25 0 0 1 0 0 0 0 0999 V2000 0.3893 -4.1213 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 -2.6559 -2.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 -0.0000 -2.0000 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 -1.2838 -3.6730 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 -1.0249 -2.7071 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 -0.8355 -5.3461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5767 -4.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 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 -1.8014 -5.6049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 1 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 0.0000 -0.0000 0.0000 C 0 0 1 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 -2.0602 -6.5708 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5085 -4.8978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 4 19 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 16 1 0 0 0 0 8 10 1 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 14 1 0 0 0 0 10 18 1 0 0 0 0 11 19 1 0 0 0 0 12 13 2 0 0 0 0 12 17 1 0 0 0 0 14 18 1 1 0 0 0 15 18 1 1 0 0 0 15 19 1 0 0 0 0 16 20 1 6 0 0 0 16 21 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 3 1 1 0 0 0 19 20 1 1 0 0 0 20 5 1 1 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	338.25
Volume:	367.251
LogP:	3.075
LogD:	2.048
LogS:	-3.231
# Rotatable Bonds:	4
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.682
Synthetic Accessibility Score:	4.429
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.947
MDCK Permeability:	2.311183197889477e-05
Pgp-inhibitor:	0.964
Pgp-substrate:	0.328
Human Intestinal Absorption (HIA):	0.081
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.826
Plasma Protein Binding (PPB):	84.88168334960938%
Volume Distribution (VD):	0.441
Pgp-substrate:	16.504026412963867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.058
CYP1A2-substrate:	0.378
CYP2C19-inhibitor:	0.027
CYP2C19-substrate:	0.501
CYP2C9-inhibitor:	0.165
CYP2C9-substrate:	0.263
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.151
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.15

ADMET: Excretion

Clearance (CL):	2.412
Half-life (T1/2):	0.792

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.384
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.109
Skin Sensitization:	0.946
Carcinogencity:	0.074
Eye Corrosion:	0.721
Eye Irritation:	0.891
Respiratory Toxicity:	0.56

Download Data

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

Natural Product: NPC475069

Natural Product ID:	NPC475069
*Common Name:**	3,4-Dihydroxyclerodan-13Z-En-15-Oic Acid
IUPAC Name:	(Z)-5-[(1R,2S,4aR,5S,6R,8aS)-5,6-dihydroxy-1,2,4a,5-tetramethyl-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]-3-methylpent-2-enoic acid
Synonyms:
Standard InCHIKey:	JWWWAEIMVGEDRK-DWZNYUOSSA-N
Standard InCHI:	InChI=1S/C20H34O4/c1-13(12-17(22)23)8-10-18(3)14(2)9-11-19(4)15(18)6-7-16(21)20(19,5)24/h12,14-16,21,24H,6-11H2,1-5H3,(H,22,23)/b13-12-/t14-,15-,16+,18+,19+,20+/m0/s1
SMILES:	CC1CCC2(C(C1(C)CCC(=CC(=O)O)C)CCC(C2(C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495656
PubChem CID:	11624227
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
NPO2430	Detarium microcarpum	Species	Fabaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16724838]
NPO2430	Detarium microcarpum	Species	Fabaceae	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
Others	2

Activity Type	# Activity
Individual Protein	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Activity	=	10.0	ug	PMID[463840]
NPT985	Organism	Cladosporium cucumerinum	Cladosporium cucumerinum	Activity	=	10.0	ug	PMID[463840]

☑ 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 NPC475069 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	185
0.1-0.2	1183
0.2-0.3	4419
0.3-0.4	11746
0.4-0.5	11361
0.5-0.6	6466
0.6-0.7	5285
0.7-0.8	1904
0.8-0.85	119
0.85-0.9	21
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC175145
0.95	High Similarity	NPC2524
0.925	High Similarity	NPC281880
0.9146	High Similarity	NPC476927
0.9136	High Similarity	NPC159148
0.8916	High Similarity	NPC79945
0.8902	High Similarity	NPC170303
0.8875	High Similarity	NPC132542
0.881	High Similarity	NPC306951
0.8795	High Similarity	NPC256112
0.8736	High Similarity	NPC82876
0.8706	High Similarity	NPC109528
0.8667	High Similarity	NPC53565
0.8652	High Similarity	NPC53555
0.8636	High Similarity	NPC78973
0.8621	High Similarity	NPC104560
0.8556	High Similarity	NPC119562
0.8556	High Similarity	NPC279410
0.8523	High Similarity	NPC314727
0.8523	High Similarity	NPC262858
0.8523	High Similarity	NPC472240
0.8506	High Similarity	NPC245004
0.8506	High Similarity	NPC166857
0.85	High Similarity	NPC201048
0.85	High Similarity	NPC476366
0.8495	Intermediate Similarity	NPC38855
0.8444	Intermediate Similarity	NPC476304
0.8415	Intermediate Similarity	NPC470711
0.8415	Intermediate Similarity	NPC470758
0.8391	Intermediate Similarity	NPC131813
0.8372	Intermediate Similarity	NPC130966
0.8372	Intermediate Similarity	NPC102048
0.8372	Intermediate Similarity	NPC302360
0.837	Intermediate Similarity	NPC473153
0.8352	Intermediate Similarity	NPC105490
0.8352	Intermediate Similarity	NPC476186
0.8333	Intermediate Similarity	NPC329842
0.8333	Intermediate Similarity	NPC74296
0.8333	Intermediate Similarity	NPC110923
0.8315	Intermediate Similarity	NPC20946
0.8315	Intermediate Similarity	NPC170633
0.8315	Intermediate Similarity	NPC146554
0.8298	Intermediate Similarity	NPC474190
0.8293	Intermediate Similarity	NPC470749
0.828	Intermediate Similarity	NPC210337
0.828	Intermediate Similarity	NPC99726
0.8276	Intermediate Similarity	NPC35933
0.8261	Intermediate Similarity	NPC276110
0.8261	Intermediate Similarity	NPC472441
0.8256	Intermediate Similarity	NPC23748
0.8256	Intermediate Similarity	NPC57370
0.825	Intermediate Similarity	NPC167706
0.8242	Intermediate Similarity	NPC38232
0.8242	Intermediate Similarity	NPC7349
0.8242	Intermediate Similarity	NPC275809
0.8242	Intermediate Similarity	NPC214697
0.8229	Intermediate Similarity	NPC475050
0.8211	Intermediate Similarity	NPC11974
0.8202	Intermediate Similarity	NPC291665
0.8202	Intermediate Similarity	NPC229612
0.8202	Intermediate Similarity	NPC7280
0.8191	Intermediate Similarity	NPC247233
0.8191	Intermediate Similarity	NPC218107
0.8182	Intermediate Similarity	NPC73038
0.8182	Intermediate Similarity	NPC473226
0.8172	Intermediate Similarity	NPC114743
0.8172	Intermediate Similarity	NPC250757
0.8172	Intermediate Similarity	NPC301534
0.8172	Intermediate Similarity	NPC88009
0.8172	Intermediate Similarity	NPC195366
0.8171	Intermediate Similarity	NPC32832
0.8152	Intermediate Similarity	NPC215700
0.8152	Intermediate Similarity	NPC87095
0.8152	Intermediate Similarity	NPC470958
0.8152	Intermediate Similarity	NPC472976
0.8152	Intermediate Similarity	NPC472977
0.8152	Intermediate Similarity	NPC470957
0.8132	Intermediate Similarity	NPC472811
0.8132	Intermediate Similarity	NPC25299
0.8132	Intermediate Similarity	NPC84319
0.8132	Intermediate Similarity	NPC235884
0.8132	Intermediate Similarity	NPC306541
0.8132	Intermediate Similarity	NPC189520
0.8132	Intermediate Similarity	NPC212948
0.8132	Intermediate Similarity	NPC52021
0.8132	Intermediate Similarity	NPC71074
0.8132	Intermediate Similarity	NPC472149
0.8132	Intermediate Similarity	NPC300351
0.8125	Intermediate Similarity	NPC283343
0.8125	Intermediate Similarity	NPC273668
0.8125	Intermediate Similarity	NPC258547
0.8125	Intermediate Similarity	NPC472815
0.8111	Intermediate Similarity	NPC16265
0.8111	Intermediate Similarity	NPC246028
0.8105	Intermediate Similarity	NPC473510
0.8105	Intermediate Similarity	NPC324841
0.8105	Intermediate Similarity	NPC470074
0.8105	Intermediate Similarity	NPC230546
0.8095	Intermediate Similarity	NPC167891
0.8095	Intermediate Similarity	NPC83351
0.809	Intermediate Similarity	NPC131329
0.809	Intermediate Similarity	NPC473891
0.809	Intermediate Similarity	NPC476948
0.809	Intermediate Similarity	NPC470620
0.8085	Intermediate Similarity	NPC474938
0.8085	Intermediate Similarity	NPC474785
0.8085	Intermediate Similarity	NPC231751
0.8072	Intermediate Similarity	NPC265588
0.8068	Intermediate Similarity	NPC164424
0.8068	Intermediate Similarity	NPC474013
0.8061	Intermediate Similarity	NPC186668
0.8049	Intermediate Similarity	NPC306727
0.8046	Intermediate Similarity	NPC49208
0.8046	Intermediate Similarity	NPC207013
0.8046	Intermediate Similarity	NPC317458
0.8046	Intermediate Similarity	NPC311070
0.8046	Intermediate Similarity	NPC474634
0.8043	Intermediate Similarity	NPC307335
0.8043	Intermediate Similarity	NPC136313
0.8043	Intermediate Similarity	NPC474806
0.8043	Intermediate Similarity	NPC74855
0.8043	Intermediate Similarity	NPC133579
0.8043	Intermediate Similarity	NPC472812
0.8041	Intermediate Similarity	NPC281378
0.8025	Intermediate Similarity	NPC471271
0.8025	Intermediate Similarity	NPC471268
0.8023	Intermediate Similarity	NPC142163
0.8022	Intermediate Similarity	NPC49320
0.8021	Intermediate Similarity	NPC96784
0.8021	Intermediate Similarity	NPC472554
0.8021	Intermediate Similarity	NPC303559
0.8021	Intermediate Similarity	NPC473160
0.8021	Intermediate Similarity	NPC235920
0.8021	Intermediate Similarity	NPC282524
0.8	Intermediate Similarity	NPC242767
0.8	Intermediate Similarity	NPC124512
0.8	Intermediate Similarity	NPC159763
0.8	Intermediate Similarity	NPC133588
0.8	Intermediate Similarity	NPC325229
0.8	Intermediate Similarity	NPC48107
0.8	Intermediate Similarity	NPC474668
0.8	Intermediate Similarity	NPC278673
0.8	Intermediate Similarity	NPC93411
0.8	Intermediate Similarity	NPC275086
0.8	Intermediate Similarity	NPC278386
0.8	Intermediate Similarity	NPC478056
0.798	Intermediate Similarity	NPC473284
0.798	Intermediate Similarity	NPC67321
0.798	Intermediate Similarity	NPC471205
0.798	Intermediate Similarity	NPC187435
0.7979	Intermediate Similarity	NPC158371
0.7979	Intermediate Similarity	NPC207922
0.7979	Intermediate Similarity	NPC190713
0.7979	Intermediate Similarity	NPC259733
0.7978	Intermediate Similarity	NPC82979
0.7978	Intermediate Similarity	NPC322159
0.7978	Intermediate Similarity	NPC179591
0.7978	Intermediate Similarity	NPC474970
0.7976	Intermediate Similarity	NPC91594
0.7976	Intermediate Similarity	NPC283619
0.7976	Intermediate Similarity	NPC40049
0.7976	Intermediate Similarity	NPC477924
0.7976	Intermediate Similarity	NPC470428
0.7957	Intermediate Similarity	NPC32407
0.7957	Intermediate Similarity	NPC20235
0.7957	Intermediate Similarity	NPC88116
0.7957	Intermediate Similarity	NPC282395
0.7957	Intermediate Similarity	NPC231063
0.7957	Intermediate Similarity	NPC145667
0.7957	Intermediate Similarity	NPC263548
0.7957	Intermediate Similarity	NPC299100
0.7957	Intermediate Similarity	NPC57117
0.7957	Intermediate Similarity	NPC299996
0.7955	Intermediate Similarity	NPC185568
0.7952	Intermediate Similarity	NPC477923
0.7952	Intermediate Similarity	NPC66566
0.7938	Intermediate Similarity	NPC470571
0.7938	Intermediate Similarity	NPC109195
0.7938	Intermediate Similarity	NPC477915
0.7938	Intermediate Similarity	NPC11956
0.7938	Intermediate Similarity	NPC472552
0.7938	Intermediate Similarity	NPC475038
0.7935	Intermediate Similarity	NPC473675
0.7935	Intermediate Similarity	NPC158030
0.7935	Intermediate Similarity	NPC472978
0.7935	Intermediate Similarity	NPC116726
0.7935	Intermediate Similarity	NPC145067
0.7935	Intermediate Similarity	NPC65120
0.7935	Intermediate Similarity	NPC233455
0.7935	Intermediate Similarity	NPC4036
0.7935	Intermediate Similarity	NPC72845
0.7931	Intermediate Similarity	NPC296701
0.7931	Intermediate Similarity	NPC224455
0.7931	Intermediate Similarity	NPC30166
0.7931	Intermediate Similarity	NPC47763
0.7931	Intermediate Similarity	NPC155521
0.7931	Intermediate Similarity	NPC218616
0.7917	Intermediate Similarity	NPC251680
0.7917	Intermediate Similarity	NPC472826
0.7917	Intermediate Similarity	NPC266955

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 NPC475069 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1510
0.2-0.3	3854
0.3-0.4	2406
0.4-0.5	767
0.5-0.6	199
0.6-0.7	229
0.7-0.8	24
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
0.8	Intermediate Similarity	NPD4225	Approved
0.7935	Intermediate Similarity	NPD7515	Phase 2
0.7917	Intermediate Similarity	NPD7639	Approved
0.7917	Intermediate Similarity	NPD7640	Approved
0.7812	Intermediate Similarity	NPD7638	Approved
0.7701	Intermediate Similarity	NPD7525	Registered
0.7579	Intermediate Similarity	NPD7748	Approved
0.7475	Intermediate Similarity	NPD5344	Discontinued
0.7391	Intermediate Similarity	NPD3618	Phase 1
0.7386	Intermediate Similarity	NPD7645	Phase 2
0.7347	Intermediate Similarity	NPD7902	Approved
0.734	Intermediate Similarity	NPD5328	Approved
0.7315	Intermediate Similarity	NPD7115	Discovery
0.7241	Intermediate Similarity	NPD6933	Approved
0.7228	Intermediate Similarity	NPD7632	Discontinued
0.7188	Intermediate Similarity	NPD6079	Approved
0.7184	Intermediate Similarity	NPD7128	Approved
0.7184	Intermediate Similarity	NPD6675	Approved
0.7184	Intermediate Similarity	NPD6402	Approved
0.7184	Intermediate Similarity	NPD5739	Approved
0.7182	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7524	Approved
0.7126	Intermediate Similarity	NPD7339	Approved
0.7126	Intermediate Similarity	NPD8264	Approved
0.7126	Intermediate Similarity	NPD6942	Approved
0.7113	Intermediate Similarity	NPD4202	Approved
0.7097	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7327	Approved
0.7091	Intermediate Similarity	NPD7328	Approved
0.7059	Intermediate Similarity	NPD5211	Phase 2
0.7048	Intermediate Similarity	NPD7320	Approved
0.7048	Intermediate Similarity	NPD6881	Approved
0.7048	Intermediate Similarity	NPD6899	Approved
0.7045	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7900	Approved
0.703	Intermediate Similarity	NPD6648	Approved
0.7011	Intermediate Similarity	NPD6926	Approved
0.7011	Intermediate Similarity	NPD6924	Approved
0.7	Intermediate Similarity	NPD6083	Phase 2
0.7	Intermediate Similarity	NPD6084	Phase 2
0.7	Intermediate Similarity	NPD4755	Approved
0.6989	Remote Similarity	NPD3133	Approved
0.6989	Remote Similarity	NPD3665	Phase 1
0.6989	Remote Similarity	NPD3666	Approved
0.6989	Remote Similarity	NPD4786	Approved
0.6981	Remote Similarity	NPD6373	Approved
0.6981	Remote Similarity	NPD6372	Approved
0.6979	Remote Similarity	NPD6051	Approved
0.6964	Remote Similarity	NPD8377	Approved
0.6964	Remote Similarity	NPD8294	Approved
0.6957	Remote Similarity	NPD3667	Approved
0.6957	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5701	Approved
0.6952	Remote Similarity	NPD5697	Approved
0.6947	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8297	Approved
0.6939	Remote Similarity	NPD6399	Phase 3
0.6923	Remote Similarity	NPD6930	Phase 2
0.6923	Remote Similarity	NPD5141	Approved
0.6923	Remote Similarity	NPD6931	Approved
0.6916	Remote Similarity	NPD6883	Approved
0.6916	Remote Similarity	NPD7290	Approved
0.6916	Remote Similarity	NPD7102	Approved
0.6903	Remote Similarity	NPD8033	Approved
0.6903	Remote Similarity	NPD8378	Approved
0.6903	Remote Similarity	NPD8380	Approved
0.6903	Remote Similarity	NPD8296	Approved
0.6903	Remote Similarity	NPD8379	Approved
0.6903	Remote Similarity	NPD8335	Approved
0.69	Remote Similarity	NPD5221	Approved
0.69	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5222	Approved
0.69	Remote Similarity	NPD4697	Phase 3
0.6889	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6011	Approved
0.6887	Remote Similarity	NPD6686	Approved
0.6882	Remote Similarity	NPD6695	Phase 3
0.6881	Remote Similarity	NPD4632	Approved
0.6863	Remote Similarity	NPD5285	Approved
0.6863	Remote Similarity	NPD5286	Approved
0.6863	Remote Similarity	NPD4700	Approved
0.6863	Remote Similarity	NPD4696	Approved
0.6852	Remote Similarity	NPD8130	Phase 1
0.6852	Remote Similarity	NPD6650	Approved
0.6852	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD6617	Approved
0.6852	Remote Similarity	NPD6869	Approved
0.6852	Remote Similarity	NPD6649	Approved
0.6852	Remote Similarity	NPD6847	Approved
0.6842	Remote Similarity	NPD5330	Approved
0.6842	Remote Similarity	NPD7521	Approved
0.6842	Remote Similarity	NPD4623	Approved
0.6842	Remote Similarity	NPD6684	Approved
0.6842	Remote Similarity	NPD7146	Approved
0.6842	Remote Similarity	NPD4519	Discontinued
0.6842	Remote Similarity	NPD7334	Approved
0.6842	Remote Similarity	NPD6409	Approved
0.6837	Remote Similarity	NPD7637	Suspended
0.6832	Remote Similarity	NPD5173	Approved
0.6822	Remote Similarity	NPD6014	Approved
0.6822	Remote Similarity	NPD6013	Approved
0.6822	Remote Similarity	NPD6012	Approved
0.6813	Remote Similarity	NPD4195	Approved
0.6813	Remote Similarity	NPD6929	Approved
0.6809	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4753	Phase 2
0.6796	Remote Similarity	NPD5223	Approved
0.6789	Remote Similarity	NPD6882	Approved
0.6771	Remote Similarity	NPD3573	Approved
0.6759	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD7503	Approved
0.6739	Remote Similarity	NPD7332	Phase 2
0.6739	Remote Similarity	NPD7509	Discontinued
0.6739	Remote Similarity	NPD7514	Phase 3
0.6731	Remote Similarity	NPD4633	Approved
0.6731	Remote Similarity	NPD5224	Approved
0.6731	Remote Similarity	NPD5225	Approved
0.6731	Remote Similarity	NPD5226	Approved
0.6707	Remote Similarity	NPD368	Approved
0.6703	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5737	Approved
0.6701	Remote Similarity	NPD6903	Approved
0.6701	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5174	Approved
0.6667	Remote Similarity	NPD7507	Approved
0.6634	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD5695	Phase 3
0.6633	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD4634	Approved
0.6602	Remote Similarity	NPD5696	Approved
0.6602	Remote Similarity	NPD5290	Discontinued
0.66	Remote Similarity	NPD5779	Approved
0.66	Remote Similarity	NPD5778	Approved
0.6598	Remote Similarity	NPD7750	Discontinued
0.6596	Remote Similarity	NPD4223	Phase 3
0.6596	Remote Similarity	NPD4221	Approved
0.6593	Remote Similarity	NPD6925	Approved
0.6593	Remote Similarity	NPD5776	Phase 2
0.6591	Remote Similarity	NPD4243	Approved
0.6591	Remote Similarity	NPD7151	Approved
0.6591	Remote Similarity	NPD7152	Approved
0.6591	Remote Similarity	NPD7150	Approved
0.6574	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1696	Phase 3
0.6562	Remote Similarity	NPD1694	Approved
0.6562	Remote Similarity	NPD6893	Approved
0.6562	Remote Similarity	NPD5329	Approved
0.6559	Remote Similarity	NPD4821	Approved
0.6559	Remote Similarity	NPD4695	Discontinued
0.6559	Remote Similarity	NPD4822	Approved
0.6559	Remote Similarity	NPD4819	Approved
0.6559	Remote Similarity	NPD4820	Approved
0.6552	Remote Similarity	NPD6922	Approved
0.6552	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6923	Approved
0.6549	Remote Similarity	NPD6009	Approved
0.6542	Remote Similarity	NPD4767	Approved
0.6542	Remote Similarity	NPD4768	Approved
0.6522	Remote Similarity	NPD6319	Approved
0.6522	Remote Similarity	NPD7145	Approved
0.6514	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5281	Approved
0.65	Remote Similarity	NPD5284	Approved
0.65	Remote Similarity	NPD7319	Approved
0.65	Remote Similarity	NPD6411	Approved
0.6495	Remote Similarity	NPD5279	Phase 3
0.6491	Remote Similarity	NPD6335	Approved
0.6489	Remote Similarity	NPD6898	Phase 1
0.6489	Remote Similarity	NPD6902	Approved
0.6484	Remote Similarity	NPD6117	Approved
0.6481	Remote Similarity	NPD6412	Phase 2
0.6481	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7144	Approved
0.6477	Remote Similarity	NPD7143	Approved
0.6471	Remote Similarity	NPD5210	Approved
0.6471	Remote Similarity	NPD4629	Approved
0.6465	Remote Similarity	NPD6904	Approved
0.6465	Remote Similarity	NPD6673	Approved
0.6465	Remote Similarity	NPD6080	Approved
0.646	Remote Similarity	NPD6868	Approved
0.646	Remote Similarity	NPD6274	Approved
0.6458	Remote Similarity	NPD4197	Approved
0.6458	Remote Similarity	NPD3668	Phase 3
0.6444	Remote Similarity	NPD4785	Approved
0.6444	Remote Similarity	NPD4784	Approved
0.6435	Remote Similarity	NPD7100	Approved
0.6435	Remote Similarity	NPD7101	Approved
0.6422	Remote Similarity	NPD4729	Approved
0.6422	Remote Similarity	NPD4730	Approved
0.6422	Remote Similarity	NPD5128	Approved
0.6413	Remote Similarity	NPD6116	Phase 1

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