NPASS Compound

Structure

NPC133579 OpenBabel07101718242D 34 38 0 0 1 0 0 0 0 0999 V2000 -4.4713 -0.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9921 1.0803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5058 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0186 -0.6177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6876 -2.9231 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5315 -2.4359 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5315 2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2191 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 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 -2.5315 1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 -3.8974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3753 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 22 1 0 0 0 0 10 11 1 0 0 0 0 10 21 2 0 0 0 0 11 29 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 15 1 0 0 0 0 13 28 1 0 0 0 0 14 30 1 0 0 0 0 15 30 1 0 0 0 0 16 19 1 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 30 1 6 0 0 0 20 23 1 0 0 0 0 20 31 1 6 0 0 0 21 26 1 0 0 0 0 21 27 1 0 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 23 32 1 6 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	511.905
LogP:	5.565
LogD:	4.151
LogS:	-4.489
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.403
Synthetic Accessibility Score:	5.049
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.307
MDCK Permeability:	1.3234511243354063e-05
Pgp-inhibitor:	0.056
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.88
30% Bioavailability (F30%):	0.151

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.625
Plasma Protein Binding (PPB):	93.48131561279297%
Volume Distribution (VD):	0.615
Pgp-substrate:	9.704593658447266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.339
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.765
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.704
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.063
CYP3A4-inhibitor:	0.359
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	1.554
Half-life (T1/2):	0.039

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.39
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.803
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.065
Carcinogencity:	0.803
Eye Corrosion:	0.081
Eye Irritation:	0.129
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC133579

Natural Product ID:	NPC133579
*Common Name:**	2Alpha,3Alpha-Dihydroxyolea-5,12-Dien-28-Oic Acid
IUPAC Name:	(4aS,6aS,6aS,6bR,10S,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,10,11,12,13,14b-dodecahydropicene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	KNEXUHUBWRLDNK-MKLORTINSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-25(2)12-14-30(24(33)34)15-13-28(6)18(19(30)16-25)8-9-22-27(5)17-20(31)23(32)26(3,4)21(27)10-11-29(22,28)7/h8,10,19-20,22-23,31-32H,9,11-17H2,1-7H3,(H,33,34)/t19-,20+,22+,23+,27-,28+,29+,30-/m0/s1
SMILES:	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@H]([C@H](C(C)(C)C5=CC[C@@]34C)O)O)[C@@H]2C1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519321
PubChem CID:	44576059
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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	Species	Lamiaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	18.7	%	PMID[478484]

☑ 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 NPC133579 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	208
0.1-0.2	1245
0.2-0.3	4468
0.3-0.4	12838
0.4-0.5	10274
0.5-0.6	5814
0.6-0.7	4968
0.7-0.8	2383
0.8-0.85	240
0.85-0.9	151
0.9-0.95	105
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474806
0.9773	High Similarity	NPC32118
0.9655	High Similarity	NPC52021
0.9655	High Similarity	NPC300351
0.9655	High Similarity	NPC71074
0.9655	High Similarity	NPC235884
0.9655	High Similarity	NPC25299
0.9655	High Similarity	NPC84319
0.9655	High Similarity	NPC472149
0.9655	High Similarity	NPC306541
0.9551	High Similarity	NPC96916
0.9545	High Similarity	NPC136313
0.9545	High Similarity	NPC275809
0.9545	High Similarity	NPC74855
0.9545	High Similarity	NPC307335
0.954	High Similarity	NPC49320
0.9444	High Similarity	NPC88847
0.9444	High Similarity	NPC173744
0.9444	High Similarity	NPC207922
0.9444	High Similarity	NPC73004
0.9444	High Similarity	NPC204961
0.9444	High Similarity	NPC158371
0.9444	High Similarity	NPC259733
0.9438	High Similarity	NPC20235
0.9438	High Similarity	NPC32407
0.9438	High Similarity	NPC231063
0.9438	High Similarity	NPC145667
0.9438	High Similarity	NPC282395
0.9438	High Similarity	NPC87095
0.9438	High Similarity	NPC88116
0.9438	High Similarity	NPC263548
0.9438	High Similarity	NPC299996
0.9425	High Similarity	NPC274330
0.9425	High Similarity	NPC143232
0.9425	High Similarity	NPC198664
0.9419	High Similarity	NPC71507
0.9341	High Similarity	NPC259788
0.9341	High Similarity	NPC43686
0.9341	High Similarity	NPC247139
0.9341	High Similarity	NPC9613
0.9341	High Similarity	NPC255589
0.9333	High Similarity	NPC198245
0.9318	High Similarity	NPC126369
0.9318	High Similarity	NPC470589
0.9318	High Similarity	NPC111110
0.931	High Similarity	NPC474512
0.931	High Similarity	NPC473242
0.931	High Similarity	NPC17733
0.931	High Similarity	NPC182797
0.931	High Similarity	NPC181225
0.931	High Similarity	NPC290690
0.931	High Similarity	NPC52169
0.931	High Similarity	NPC470629
0.9239	High Similarity	NPC29765
0.9239	High Similarity	NPC271614
0.9239	High Similarity	NPC111214
0.9231	High Similarity	NPC230151
0.9231	High Similarity	NPC19376
0.9231	High Similarity	NPC201657
0.9231	High Similarity	NPC305464
0.9231	High Similarity	NPC307282
0.9231	High Similarity	NPC25848
0.9222	High Similarity	NPC80365
0.9222	High Similarity	NPC188102
0.9213	High Similarity	NPC301244
0.9213	High Similarity	NPC187722
0.9205	High Similarity	NPC290972
0.9205	High Similarity	NPC25906
0.9205	High Similarity	NPC293048
0.9205	High Similarity	NPC127689
0.9205	High Similarity	NPC64872
0.9205	High Similarity	NPC130520
0.9205	High Similarity	NPC121798
0.9205	High Similarity	NPC263393
0.9205	High Similarity	NPC270768
0.9205	High Similarity	NPC61543
0.9205	High Similarity	NPC59263
0.9205	High Similarity	NPC225585
0.9205	High Similarity	NPC234346
0.9205	High Similarity	NPC470588
0.9195	High Similarity	NPC130577
0.9195	High Similarity	NPC98442
0.9195	High Similarity	NPC293564
0.9195	High Similarity	NPC242468
0.9195	High Similarity	NPC171203
0.9195	High Similarity	NPC68160
0.9195	High Similarity	NPC307426
0.9195	High Similarity	NPC102683
0.9195	High Similarity	NPC88716
0.9195	High Similarity	NPC142415
0.9195	High Similarity	NPC51700
0.9195	High Similarity	NPC18064
0.914	High Similarity	NPC35239
0.913	High Similarity	NPC106112
0.913	High Similarity	NPC261935
0.9111	High Similarity	NPC118519
0.9111	High Similarity	NPC202728
0.9111	High Similarity	NPC229281
0.9111	High Similarity	NPC158059
0.9101	High Similarity	NPC210037
0.9101	High Similarity	NPC18872
0.9101	High Similarity	NPC120968
0.9101	High Similarity	NPC290614
0.9101	High Similarity	NPC291028
0.9101	High Similarity	NPC7260
0.9101	High Similarity	NPC227467
0.9101	High Similarity	NPC273621
0.9101	High Similarity	NPC130278
0.9101	High Similarity	NPC474728
0.9101	High Similarity	NPC477872
0.9091	High Similarity	NPC40552
0.9091	High Similarity	NPC246708
0.908	High Similarity	NPC56588
0.908	High Similarity	NPC72638
0.907	High Similarity	NPC171789
0.9043	High Similarity	NPC233012
0.9043	High Similarity	NPC54909
0.9043	High Similarity	NPC256247
0.9032	High Similarity	NPC188833
0.9011	High Similarity	NPC296164
0.9011	High Similarity	NPC191412
0.9011	High Similarity	NPC209868
0.9011	High Similarity	NPC159365
0.9011	High Similarity	NPC114159
0.9011	High Similarity	NPC6818
0.9	High Similarity	NPC470590
0.9	High Similarity	NPC324341
0.9	High Similarity	NPC189520
0.9	High Similarity	NPC285184
0.9	High Similarity	NPC145067
0.9	High Similarity	NPC966
0.9	High Similarity	NPC38754
0.9	High Similarity	NPC158030
0.9	High Similarity	NPC4036
0.9	High Similarity	NPC233455
0.9	High Similarity	NPC288833
0.9	High Similarity	NPC228784
0.9	High Similarity	NPC155120
0.9	High Similarity	NPC60755
0.9	High Similarity	NPC65120
0.9	High Similarity	NPC77099
0.9	High Similarity	NPC282616
0.9	High Similarity	NPC474525
0.9	High Similarity	NPC105189
0.8989	High Similarity	NPC161751
0.8989	High Similarity	NPC95246
0.8989	High Similarity	NPC474972
0.8989	High Similarity	NPC474686
0.8977	High Similarity	NPC477926
0.8925	High Similarity	NPC203343
0.8925	High Similarity	NPC21728
0.8925	High Similarity	NPC312075
0.8913	High Similarity	NPC473240
0.8913	High Similarity	NPC53565
0.8901	High Similarity	NPC298554
0.8901	High Similarity	NPC86368
0.8901	High Similarity	NPC295643
0.8901	High Similarity	NPC272075
0.8901	High Similarity	NPC214756
0.8889	High Similarity	NPC46441
0.8889	High Similarity	NPC193750
0.8889	High Similarity	NPC172361
0.8889	High Similarity	NPC120840
0.8889	High Similarity	NPC86372
0.8889	High Similarity	NPC113989
0.8864	High Similarity	NPC324063
0.8864	High Similarity	NPC73038
0.8817	High Similarity	NPC9487
0.8817	High Similarity	NPC476327
0.8817	High Similarity	NPC132824
0.8817	High Similarity	NPC62516
0.8817	High Similarity	NPC157113
0.8817	High Similarity	NPC116457
0.8817	High Similarity	NPC327179
0.8817	High Similarity	NPC476318
0.8817	High Similarity	NPC473158
0.8804	High Similarity	NPC222047
0.8804	High Similarity	NPC91010
0.8804	High Similarity	NPC474529
0.8791	High Similarity	NPC6255
0.8791	High Similarity	NPC235704
0.8791	High Similarity	NPC471588
0.8791	High Similarity	NPC475708
0.8778	High Similarity	NPC30522
0.8764	High Similarity	NPC73064
0.8763	High Similarity	NPC284865
0.875	High Similarity	NPC133954
0.8723	High Similarity	NPC189880
0.8723	High Similarity	NPC187933
0.8721	High Similarity	NPC473420
0.871	High Similarity	NPC139570
0.871	High Similarity	NPC195715
0.871	High Similarity	NPC474727
0.871	High Similarity	NPC148523
0.8696	High Similarity	NPC49776
0.8696	High Similarity	NPC118490
0.8696	High Similarity	NPC474436
0.8696	High Similarity	NPC63118
0.8667	High Similarity	NPC242864
0.8667	High Similarity	NPC474511

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 NPC133579 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1600
0.2-0.3	3719
0.3-0.4	2408
0.4-0.5	756
0.5-0.6	216
0.6-0.7	199
0.7-0.8	64
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD7515	Phase 2
0.8602	High Similarity	NPD7748	Approved
0.8333	Intermediate Similarity	NPD7902	Approved
0.8132	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8022	Intermediate Similarity	NPD4786	Approved
0.8021	Intermediate Similarity	NPD7900	Approved
0.8021	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3667	Approved
0.7979	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6399	Phase 3
0.7865	Intermediate Similarity	NPD7645	Phase 2
0.7849	Intermediate Similarity	NPD3618	Phase 1
0.7789	Intermediate Similarity	NPD5328	Approved
0.7714	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD6079	Approved
0.7629	Intermediate Similarity	NPD8035	Phase 2
0.7629	Intermediate Similarity	NPD6411	Approved
0.7629	Intermediate Similarity	NPD8034	Phase 2
0.7525	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD7639	Approved
0.7451	Intermediate Similarity	NPD7640	Approved
0.7447	Intermediate Similarity	NPD3665	Phase 1
0.7447	Intermediate Similarity	NPD3666	Approved
0.7447	Intermediate Similarity	NPD3668	Phase 3
0.7447	Intermediate Similarity	NPD3133	Approved
0.7429	Intermediate Similarity	NPD6675	Approved
0.7429	Intermediate Similarity	NPD7128	Approved
0.7429	Intermediate Similarity	NPD6402	Approved
0.7429	Intermediate Similarity	NPD5739	Approved
0.7423	Intermediate Similarity	NPD6101	Approved
0.7423	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7525	Registered
0.7387	Intermediate Similarity	NPD7115	Discovery
0.7374	Intermediate Similarity	NPD4202	Approved
0.7333	Intermediate Similarity	NPD6117	Approved
0.7327	Intermediate Similarity	NPD5222	Approved
0.7327	Intermediate Similarity	NPD5221	Approved
0.7327	Intermediate Similarity	NPD4697	Phase 3
0.7327	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7614	Phase 1
0.7292	Intermediate Similarity	NPD6684	Approved
0.7292	Intermediate Similarity	NPD5330	Approved
0.7292	Intermediate Similarity	NPD7146	Approved
0.7292	Intermediate Similarity	NPD6409	Approved
0.7292	Intermediate Similarity	NPD7521	Approved
0.7292	Intermediate Similarity	NPD7334	Approved
0.729	Intermediate Similarity	NPD6881	Approved
0.729	Intermediate Similarity	NPD7320	Approved
0.729	Intermediate Similarity	NPD6899	Approved
0.7255	Intermediate Similarity	NPD6083	Phase 2
0.7255	Intermediate Similarity	NPD6084	Phase 2
0.7255	Intermediate Similarity	NPD5173	Approved
0.7255	Intermediate Similarity	NPD4755	Approved
0.7253	Intermediate Similarity	NPD6116	Phase 1
0.7232	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6942	Approved
0.7222	Intermediate Similarity	NPD7339	Approved
0.7222	Intermediate Similarity	NPD6372	Approved
0.7222	Intermediate Similarity	NPD6373	Approved
0.7216	Intermediate Similarity	NPD3573	Approved
0.7204	Intermediate Similarity	NPD4695	Discontinued
0.7196	Intermediate Similarity	NPD5697	Approved
0.7196	Intermediate Similarity	NPD5701	Approved
0.7184	Intermediate Similarity	NPD4225	Approved
0.7182	Intermediate Similarity	NPD8297	Approved
0.7174	Intermediate Similarity	NPD6118	Approved
0.7174	Intermediate Similarity	NPD6115	Approved
0.7174	Intermediate Similarity	NPD6114	Approved
0.7174	Intermediate Similarity	NPD6697	Approved
0.7156	Intermediate Similarity	NPD7290	Approved
0.7156	Intermediate Similarity	NPD6883	Approved
0.7156	Intermediate Similarity	NPD7102	Approved
0.7155	Intermediate Similarity	NPD8328	Phase 3
0.7143	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6011	Approved
0.7117	Intermediate Similarity	NPD4632	Approved
0.7115	Intermediate Similarity	NPD5285	Approved
0.7115	Intermediate Similarity	NPD4700	Approved
0.7115	Intermediate Similarity	NPD5286	Approved
0.7115	Intermediate Similarity	NPD4696	Approved
0.7113	Intermediate Similarity	NPD5279	Phase 3
0.7111	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6650	Approved
0.7091	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6869	Approved
0.7091	Intermediate Similarity	NPD6847	Approved
0.7091	Intermediate Similarity	NPD8130	Phase 1
0.7091	Intermediate Similarity	NPD6649	Approved
0.7091	Intermediate Similarity	NPD6617	Approved
0.7071	Intermediate Similarity	NPD4753	Phase 2
0.7064	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6012	Approved
0.7064	Intermediate Similarity	NPD6014	Approved
0.7064	Intermediate Similarity	NPD6013	Approved
0.7059	Intermediate Similarity	NPD5695	Phase 3
0.7048	Intermediate Similarity	NPD5223	Approved
0.7037	Intermediate Similarity	NPD6412	Phase 2
0.703	Intermediate Similarity	NPD5778	Approved
0.703	Intermediate Similarity	NPD5779	Approved
0.7027	Intermediate Similarity	NPD6882	Approved
0.699	Remote Similarity	NPD7732	Phase 3
0.6981	Remote Similarity	NPD5211	Phase 2
0.6981	Remote Similarity	NPD5226	Approved
0.6981	Remote Similarity	NPD5225	Approved
0.6981	Remote Similarity	NPD5224	Approved
0.6981	Remote Similarity	NPD4633	Approved
0.6939	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5281	Approved
0.6931	Remote Similarity	NPD5284	Approved
0.6916	Remote Similarity	NPD5175	Approved
0.6916	Remote Similarity	NPD4754	Approved
0.6916	Remote Similarity	NPD5174	Approved
0.6893	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4221	Approved
0.6875	Remote Similarity	NPD4223	Phase 3
0.6857	Remote Similarity	NPD5696	Approved
0.6852	Remote Similarity	NPD5141	Approved
0.6847	Remote Similarity	NPD4634	Approved
0.6842	Remote Similarity	NPD6868	Approved
0.6842	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5329	Approved
0.6822	Remote Similarity	NPD7632	Discontinued
0.6818	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6686	Approved
0.6814	Remote Similarity	NPD8133	Approved
0.6804	Remote Similarity	NPD4788	Approved
0.6789	Remote Similarity	NPD4768	Approved
0.6789	Remote Similarity	NPD6008	Approved
0.6789	Remote Similarity	NPD4767	Approved
0.6783	Remote Similarity	NPD6009	Approved
0.6774	Remote Similarity	NPD6933	Approved
0.6768	Remote Similarity	NPD6098	Approved
0.6752	Remote Similarity	NPD6319	Approved
0.675	Remote Similarity	NPD7507	Approved
0.6735	Remote Similarity	NPD4197	Approved
0.6733	Remote Similarity	NPD6904	Approved
0.6733	Remote Similarity	NPD6673	Approved
0.6733	Remote Similarity	NPD6080	Approved
0.6731	Remote Similarity	NPD5210	Approved
0.6731	Remote Similarity	NPD4629	Approved
0.6724	Remote Similarity	NPD6335	Approved
0.6703	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4729	Approved
0.6667	Remote Similarity	NPD4730	Approved
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD5168	Approved
0.6639	Remote Similarity	NPD7736	Approved
0.6638	Remote Similarity	NPD6317	Approved
0.6632	Remote Similarity	NPD3617	Approved
0.6632	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6050	Approved
0.66	Remote Similarity	NPD4689	Approved
0.66	Remote Similarity	NPD4519	Discontinued
0.66	Remote Similarity	NPD5280	Approved
0.66	Remote Similarity	NPD4694	Approved
0.66	Remote Similarity	NPD4693	Phase 3
0.66	Remote Similarity	NPD5205	Approved
0.66	Remote Similarity	NPD5690	Phase 2
0.66	Remote Similarity	NPD4688	Approved
0.66	Remote Similarity	NPD4138	Approved
0.66	Remote Similarity	NPD4623	Approved
0.66	Remote Similarity	NPD4690	Approved
0.6585	Remote Similarity	NPD7319	Approved
0.6583	Remote Similarity	NPD7604	Phase 2
0.6581	Remote Similarity	NPD6314	Approved
0.6581	Remote Similarity	NPD6313	Approved
0.6559	Remote Similarity	NPD6926	Approved
0.6559	Remote Similarity	NPD6924	Approved
0.6555	Remote Similarity	NPD8033	Approved
0.6555	Remote Similarity	NPD5983	Phase 2
0.6555	Remote Similarity	NPD6909	Approved
0.6555	Remote Similarity	NPD6908	Approved
0.6549	Remote Similarity	NPD5169	Approved
0.6549	Remote Similarity	NPD5251	Approved
0.6549	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD5250	Approved
0.6549	Remote Similarity	NPD5247	Approved
0.6549	Remote Similarity	NPD5135	Approved
0.6549	Remote Similarity	NPD5249	Phase 3
0.6549	Remote Similarity	NPD5248	Approved
0.6529	Remote Similarity	NPD7492	Approved
0.6525	Remote Similarity	NPD7516	Approved
0.6505	Remote Similarity	NPD5692	Phase 3
0.65	Remote Similarity	NPD1694	Approved
0.6495	Remote Similarity	NPD4748	Discontinued
0.6491	Remote Similarity	NPD5127	Approved
0.6491	Remote Similarity	NPD5217	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