NPASS Compound

Structure

NPC282395 OpenBabel07101718192D 35 39 0 0 1 0 0 0 0 0999 V2000 -1.8437 -4.1019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4339 -3.7856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0206 2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5331 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0456 2.3069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -1.9500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3775 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6887 0.9750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3775 0.9750 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3775 -0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -3.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6887 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5331 1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8444 -0.4875 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 -2.5331 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5331 3.1512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 -0.4875 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2219 1.4625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -1.4625 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 5 28 1 0 0 0 0 7 8 1 0 0 0 0 7 18 2 0 0 0 0 8 22 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 29 1 0 0 0 0 11 13 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 28 1 0 0 0 0 13 30 1 0 0 0 0 14 30 1 0 0 0 0 15 19 1 0 0 0 0 15 25 1 0 0 0 0 16 20 1 0 0 0 0 16 26 1 0 0 0 0 17 27 1 0 0 0 0 17 31 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 32 1 6 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 26 1 1 0 0 0 22 29 1 0 0 0 0 23 27 1 6 0 0 0 23 33 1 0 0 0 0 24 34 2 0 0 0 0 24 35 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 6 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.35
Volume:	523.332
LogP:	4.337
LogD:	3.707
LogS:	-3.819
# Rotatable Bonds:	2
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.402
Synthetic Accessibility Score:	4.924
Fsp3:	0.9
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:	-5.444
MDCK Permeability:	9.046687409863807e-06
Pgp-inhibitor:	0.013
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.187

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.179
Plasma Protein Binding (PPB):	92.25167846679688%
Volume Distribution (VD):	0.574
Pgp-substrate:	5.258341312408447%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.402
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.799
CYP2C9-inhibitor:	0.065
CYP2C9-substrate:	0.303
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.334
CYP3A4-substrate:	0.177

ADMET: Excretion

Clearance (CL):	2.293
Half-life (T1/2):	0.231

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.493
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.218
Maximum Recommended Daily Dose:	0.652
Skin Sensitization:	0.049
Carcinogencity:	0.271
Eye Corrosion:	0.013
Eye Irritation:	0.022
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: NPC282395

Natural Product ID:	NPC282395
*Common Name:**	2Alpha,3Alpha,24-Trihydroxyolean-12-En-28-Oic Acid
IUPAC Name:	(4aS,6aR,6aS,6bR,8aR,9S,10S,11R,12aR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	RWNHLTKFBKYDOJ-ZDNZHVAWSA-N
Standard InCHI:	InChI=1S/C30H48O5/c1-25(2)11-13-30(24(34)35)14-12-28(5)18(19(30)15-25)7-8-22-26(3)16-20(32)23(33)27(4,17-31)21(26)9-10-29(22,28)6/h7,19-23,31-33H,8-17H2,1-6H3,(H,34,35)/t19-,20+,21+,22+,23+,26-,27+,28+,29+,30-/m0/s1
SMILES:	OC[C@@]1(C)[C@H](O)[C@H](O)C[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3342058
PubChem CID:	69570248
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
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25245917]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	40500.0	nM	PMID[448573]

☑ 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 NPC282395 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	216
0.1-0.2	1337
0.2-0.3	4696
0.3-0.4	12926
0.4-0.5	10194
0.5-0.6	5561
0.6-0.7	4780
0.7-0.8	2211
0.8-0.85	437
0.85-0.9	131
0.9-0.95	147
0.95-1	61

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC88116
1.0	High Similarity	NPC299996
1.0	High Similarity	NPC263548
1.0	High Similarity	NPC32407
1.0	High Similarity	NPC231063
1.0	High Similarity	NPC20235
1.0	High Similarity	NPC145667
0.9775	High Similarity	NPC305464
0.9775	High Similarity	NPC173744
0.9775	High Similarity	NPC201657
0.9775	High Similarity	NPC204961
0.9775	High Similarity	NPC19376
0.9775	High Similarity	NPC307282
0.9775	High Similarity	NPC25848
0.9775	High Similarity	NPC73004
0.977	High Similarity	NPC472149
0.977	High Similarity	NPC235884
0.977	High Similarity	NPC71074
0.977	High Similarity	NPC25299
0.977	High Similarity	NPC84319
0.977	High Similarity	NPC300351
0.977	High Similarity	NPC52021
0.977	High Similarity	NPC306541
0.9667	High Similarity	NPC9613
0.9667	High Similarity	NPC247139
0.9667	High Similarity	NPC261935
0.9667	High Similarity	NPC106112
0.9663	High Similarity	NPC32118
0.9663	High Similarity	NPC96916
0.9659	High Similarity	NPC307335
0.9659	High Similarity	NPC275809
0.9659	High Similarity	NPC136313
0.9659	High Similarity	NPC74855
0.9655	High Similarity	NPC49320
0.9655	High Similarity	NPC130278
0.956	High Similarity	NPC29765
0.956	High Similarity	NPC111214
0.956	High Similarity	NPC271614
0.9556	High Similarity	NPC259733
0.9556	High Similarity	NPC158371
0.9556	High Similarity	NPC207922
0.954	High Similarity	NPC234346
0.954	High Similarity	NPC290972
0.954	High Similarity	NPC25906
0.954	High Similarity	NPC61543
0.954	High Similarity	NPC127689
0.954	High Similarity	NPC130520
0.954	High Similarity	NPC225585
0.954	High Similarity	NPC121798
0.954	High Similarity	NPC59263
0.954	High Similarity	NPC270768
0.954	High Similarity	NPC293048
0.954	High Similarity	NPC64872
0.954	High Similarity	NPC263393
0.9457	High Similarity	NPC35239
0.9451	High Similarity	NPC255589
0.9451	High Similarity	NPC259788
0.9451	High Similarity	NPC43686
0.9444	High Similarity	NPC198245
0.9438	High Similarity	NPC229281
0.9438	High Similarity	NPC133579
0.9438	High Similarity	NPC474806
0.9432	High Similarity	NPC126369
0.9432	High Similarity	NPC290614
0.9432	High Similarity	NPC120968
0.9432	High Similarity	NPC470589
0.9432	High Similarity	NPC227467
0.9432	High Similarity	NPC210037
0.9432	High Similarity	NPC477872
0.9432	High Similarity	NPC111110
0.9432	High Similarity	NPC18872
0.9432	High Similarity	NPC7260
0.9432	High Similarity	NPC273621
0.9425	High Similarity	NPC52169
0.9425	High Similarity	NPC182797
0.9355	High Similarity	NPC256247
0.9341	High Similarity	NPC230151
0.9341	High Similarity	NPC88847
0.9333	High Similarity	NPC6818
0.9333	High Similarity	NPC188102
0.9333	High Similarity	NPC114159
0.9333	High Similarity	NPC191412
0.9333	High Similarity	NPC87095
0.9326	High Similarity	NPC228784
0.9326	High Similarity	NPC105189
0.9326	High Similarity	NPC288833
0.9326	High Similarity	NPC324341
0.9326	High Similarity	NPC966
0.9326	High Similarity	NPC187722
0.9326	High Similarity	NPC155120
0.9326	High Similarity	NPC282616
0.9318	High Similarity	NPC274330
0.9318	High Similarity	NPC198664
0.9318	High Similarity	NPC143232
0.931	High Similarity	NPC307426
0.931	High Similarity	NPC142415
0.931	High Similarity	NPC171203
0.931	High Similarity	NPC51700
0.931	High Similarity	NPC68160
0.931	High Similarity	NPC242468
0.931	High Similarity	NPC18064
0.931	High Similarity	NPC293564
0.931	High Similarity	NPC98442
0.931	High Similarity	NPC88716
0.931	High Similarity	NPC102683
0.931	High Similarity	NPC130577
0.9239	High Similarity	NPC312075
0.9239	High Similarity	NPC203343
0.9222	High Similarity	NPC202728
0.9222	High Similarity	NPC118490
0.9222	High Similarity	NPC118519
0.9222	High Similarity	NPC86368
0.9222	High Similarity	NPC158059
0.9213	High Similarity	NPC86372
0.9213	High Similarity	NPC193750
0.9213	High Similarity	NPC172361
0.9213	High Similarity	NPC291028
0.9205	High Similarity	NPC246708
0.9205	High Similarity	NPC473242
0.9205	High Similarity	NPC470629
0.9205	High Similarity	NPC181225
0.9205	High Similarity	NPC17733
0.9205	High Similarity	NPC40552
0.9205	High Similarity	NPC474512
0.9205	High Similarity	NPC290690
0.9195	High Similarity	NPC72638
0.9149	High Similarity	NPC54909
0.9149	High Similarity	NPC233012
0.914	High Similarity	NPC188833
0.913	High Similarity	NPC476327
0.913	High Similarity	NPC132824
0.913	High Similarity	NPC476318
0.913	High Similarity	NPC116457
0.9121	High Similarity	NPC159365
0.9121	High Similarity	NPC222047
0.9121	High Similarity	NPC296164
0.9111	High Similarity	NPC145067
0.9111	High Similarity	NPC4036
0.9111	High Similarity	NPC65120
0.9111	High Similarity	NPC474525
0.9111	High Similarity	NPC475708
0.9111	High Similarity	NPC6255
0.9111	High Similarity	NPC471588
0.9111	High Similarity	NPC233455
0.9111	High Similarity	NPC38754
0.9111	High Similarity	NPC158030
0.9101	High Similarity	NPC161751
0.9101	High Similarity	NPC474972
0.9101	High Similarity	NPC470588
0.9101	High Similarity	NPC95246
0.9022	High Similarity	NPC83693
0.9022	High Similarity	NPC473240
0.9022	High Similarity	NPC148523
0.9022	High Similarity	NPC139570
0.9011	High Similarity	NPC298554
0.9011	High Similarity	NPC214756
0.9011	High Similarity	NPC272075
0.9011	High Similarity	NPC295643
0.9	High Similarity	NPC120840
0.9	High Similarity	NPC474728
0.9	High Similarity	NPC46441
0.9	High Similarity	NPC113989
0.8977	High Similarity	NPC213412
0.8969	High Similarity	NPC477877
0.8936	High Similarity	NPC164349
0.8936	High Similarity	NPC174663
0.8925	High Similarity	NPC157113
0.8925	High Similarity	NPC473158
0.8925	High Similarity	NPC98874
0.8925	High Similarity	NPC327179
0.8925	High Similarity	NPC62516
0.8913	High Similarity	NPC184006
0.8913	High Similarity	NPC209868
0.8913	High Similarity	NPC23621
0.8913	High Similarity	NPC91010
0.8913	High Similarity	NPC474529
0.8913	High Similarity	NPC80365
0.8913	High Similarity	NPC60692
0.8913	High Similarity	NPC78580
0.8901	High Similarity	NPC60755
0.8901	High Similarity	NPC470590
0.8901	High Similarity	NPC285184
0.8901	High Similarity	NPC189520
0.8901	High Similarity	NPC77099
0.8889	High Similarity	NPC474686
0.8889	High Similarity	NPC30522
0.8876	High Similarity	NPC71507
0.8876	High Similarity	NPC477926
0.8866	High Similarity	NPC284865
0.8864	High Similarity	NPC133954
0.8851	High Similarity	NPC159168
0.8851	High Similarity	NPC253402
0.8842	High Similarity	NPC476195
0.883	High Similarity	NPC476878
0.883	High Similarity	NPC187933
0.883	High Similarity	NPC476879
0.883	High Similarity	NPC189880
0.8817	High Similarity	NPC23241
0.8817	High Similarity	NPC53565
0.8817	High Similarity	NPC290481

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 NPC282395 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1724
0.2-0.3	3772
0.3-0.4	2320
0.4-0.5	673
0.5-0.6	230
0.6-0.7	179
0.7-0.8	52
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9111	High Similarity	NPD7515	Phase 2
0.871	High Similarity	NPD7748	Approved
0.8632	High Similarity	NPD7902	Approved
0.8316	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8316	Intermediate Similarity	NPD7900	Approved
0.8242	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD7645	Phase 2
0.7917	Intermediate Similarity	NPD8035	Phase 2
0.7917	Intermediate Similarity	NPD8034	Phase 2
0.7835	Intermediate Similarity	NPD6399	Phase 3
0.781	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD3618	Phase 1
0.7742	Intermediate Similarity	NPD4786	Approved
0.7717	Intermediate Similarity	NPD3667	Approved
0.7708	Intermediate Similarity	NPD5328	Approved
0.7692	Intermediate Similarity	NPD6675	Approved
0.7692	Intermediate Similarity	NPD6402	Approved
0.7692	Intermediate Similarity	NPD7128	Approved
0.7692	Intermediate Similarity	NPD5739	Approved
0.7551	Intermediate Similarity	NPD6079	Approved
0.7547	Intermediate Similarity	NPD6899	Approved
0.7547	Intermediate Similarity	NPD6881	Approved
0.7547	Intermediate Similarity	NPD7320	Approved
0.7544	Intermediate Similarity	NPD8328	Phase 3
0.7526	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD4755	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.7477	Intermediate Similarity	NPD6373	Approved
0.7477	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6372	Approved
0.7475	Intermediate Similarity	NPD4202	Approved
0.7453	Intermediate Similarity	NPD5697	Approved
0.7453	Intermediate Similarity	NPD5701	Approved
0.7451	Intermediate Similarity	NPD7638	Approved
0.7431	Intermediate Similarity	NPD8297	Approved
0.7423	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7290	Approved
0.7407	Intermediate Similarity	NPD6883	Approved
0.7407	Intermediate Similarity	NPD7102	Approved
0.7379	Intermediate Similarity	NPD7639	Approved
0.7379	Intermediate Similarity	NPD5286	Approved
0.7379	Intermediate Similarity	NPD4700	Approved
0.7379	Intermediate Similarity	NPD4696	Approved
0.7379	Intermediate Similarity	NPD7640	Approved
0.7379	Intermediate Similarity	NPD5285	Approved
0.7374	Intermediate Similarity	NPD6411	Approved
0.7368	Intermediate Similarity	NPD3665	Phase 1
0.7368	Intermediate Similarity	NPD3666	Approved
0.7368	Intermediate Similarity	NPD3133	Approved
0.7363	Intermediate Similarity	NPD6116	Phase 1
0.7353	Intermediate Similarity	NPD6083	Phase 2
0.7353	Intermediate Similarity	NPD6084	Phase 2
0.7339	Intermediate Similarity	NPD6869	Approved
0.7339	Intermediate Similarity	NPD8130	Phase 1
0.7339	Intermediate Similarity	NPD6617	Approved
0.7339	Intermediate Similarity	NPD6649	Approved
0.7339	Intermediate Similarity	NPD6847	Approved
0.7339	Intermediate Similarity	NPD6650	Approved
0.7321	Intermediate Similarity	NPD7115	Discovery
0.7315	Intermediate Similarity	NPD6012	Approved
0.7315	Intermediate Similarity	NPD6014	Approved
0.7315	Intermediate Similarity	NPD6013	Approved
0.7315	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6412	Phase 2
0.7273	Intermediate Similarity	NPD6882	Approved
0.7255	Intermediate Similarity	NPD4697	Phase 3
0.7255	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5221	Approved
0.7255	Intermediate Similarity	NPD5222	Approved
0.7253	Intermediate Similarity	NPD6117	Approved
0.7238	Intermediate Similarity	NPD5226	Approved
0.7238	Intermediate Similarity	NPD5225	Approved
0.7238	Intermediate Similarity	NPD5224	Approved
0.7238	Intermediate Similarity	NPD5211	Phase 2
0.7238	Intermediate Similarity	NPD4633	Approved
0.7222	Intermediate Similarity	NPD6011	Approved
0.7216	Intermediate Similarity	NPD6409	Approved
0.7216	Intermediate Similarity	NPD6684	Approved
0.7216	Intermediate Similarity	NPD7146	Approved
0.7216	Intermediate Similarity	NPD5330	Approved
0.7216	Intermediate Similarity	NPD7521	Approved
0.7216	Intermediate Similarity	NPD7334	Approved
0.7207	Intermediate Similarity	NPD4632	Approved
0.7188	Intermediate Similarity	NPD3668	Phase 3
0.7184	Intermediate Similarity	NPD5173	Approved
0.7182	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD4753	Phase 2
0.7172	Intermediate Similarity	NPD6101	Approved
0.717	Intermediate Similarity	NPD5174	Approved
0.717	Intermediate Similarity	NPD5175	Approved
0.7143	Intermediate Similarity	NPD3573	Approved
0.7143	Intermediate Similarity	NPD5223	Approved
0.7115	Intermediate Similarity	NPD4225	Approved
0.7103	Intermediate Similarity	NPD5141	Approved
0.7097	Intermediate Similarity	NPD6115	Approved
0.7097	Intermediate Similarity	NPD6118	Approved
0.7097	Intermediate Similarity	NPD6114	Approved
0.7097	Intermediate Similarity	NPD6697	Approved
0.7091	Intermediate Similarity	NPD4634	Approved
0.7087	Intermediate Similarity	NPD7614	Phase 1
0.7071	Intermediate Similarity	NPD6672	Approved
0.7071	Intermediate Similarity	NPD5737	Approved
0.7071	Intermediate Similarity	NPD6903	Approved
0.7064	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6686	Approved
0.7054	Intermediate Similarity	NPD8133	Approved
0.7037	Intermediate Similarity	NPD4767	Approved
0.7037	Intermediate Similarity	NPD4768	Approved
0.7033	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4754	Approved
0.699	Remote Similarity	NPD5695	Phase 3
0.6983	Remote Similarity	NPD6319	Approved
0.6975	Remote Similarity	NPD7507	Approved
0.6957	Remote Similarity	NPD6942	Approved
0.6957	Remote Similarity	NPD7339	Approved
0.6952	Remote Similarity	NPD5696	Approved
0.6947	Remote Similarity	NPD4695	Discontinued
0.6937	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6274	Approved
0.6909	Remote Similarity	NPD4729	Approved
0.6909	Remote Similarity	NPD4730	Approved
0.6909	Remote Similarity	NPD5128	Approved
0.6897	Remote Similarity	NPD7100	Approved
0.6897	Remote Similarity	NPD7101	Approved
0.6882	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6009	Approved
0.6869	Remote Similarity	NPD5279	Phase 3
0.6869	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5281	Approved
0.6863	Remote Similarity	NPD5284	Approved
0.686	Remote Similarity	NPD7736	Approved
0.6827	Remote Similarity	NPD5210	Approved
0.6827	Remote Similarity	NPD4629	Approved
0.6827	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6335	Approved
0.6804	Remote Similarity	NPD4221	Approved
0.6804	Remote Similarity	NPD4223	Phase 3
0.6803	Remote Similarity	NPD7319	Approved
0.6796	Remote Similarity	NPD5779	Approved
0.6796	Remote Similarity	NPD5778	Approved
0.6786	Remote Similarity	NPD5251	Approved
0.6786	Remote Similarity	NPD5247	Approved
0.6786	Remote Similarity	NPD5248	Approved
0.6786	Remote Similarity	NPD5250	Approved
0.6786	Remote Similarity	NPD5249	Phase 3
0.6783	Remote Similarity	NPD6868	Approved
0.678	Remote Similarity	NPD6909	Approved
0.678	Remote Similarity	NPD6908	Approved
0.6768	Remote Similarity	NPD5329	Approved
0.6762	Remote Similarity	NPD7732	Phase 3
0.6759	Remote Similarity	NPD7632	Discontinued
0.6752	Remote Similarity	NPD7516	Approved
0.675	Remote Similarity	NPD7492	Approved
0.6735	Remote Similarity	NPD4788	Approved
0.6727	Remote Similarity	NPD6008	Approved
0.6726	Remote Similarity	NPD5215	Approved
0.6726	Remote Similarity	NPD5217	Approved
0.6726	Remote Similarity	NPD5216	Approved
0.6724	Remote Similarity	NPD6317	Approved
0.67	Remote Similarity	NPD6098	Approved
0.6695	Remote Similarity	NPD6059	Approved
0.6695	Remote Similarity	NPD8377	Approved
0.6695	Remote Similarity	NPD8294	Approved
0.6695	Remote Similarity	NPD6054	Approved
0.6694	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD7604	Phase 2
0.6667	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6639	Remote Similarity	NPD5983	Phase 2
0.6639	Remote Similarity	NPD8293	Discontinued
0.6639	Remote Similarity	NPD8335	Approved
0.6639	Remote Similarity	NPD8380	Approved
0.6639	Remote Similarity	NPD7078	Approved
0.6639	Remote Similarity	NPD8033	Approved
0.6639	Remote Similarity	NPD8379	Approved
0.6639	Remote Similarity	NPD8378	Approved
0.6639	Remote Similarity	NPD8296	Approved
0.6637	Remote Similarity	NPD5135	Approved
0.6637	Remote Similarity	NPD5169	Approved
0.6637	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5168	Approved
0.6598	Remote Similarity	NPD5368	Approved
0.6593	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD6370	Approved
0.6579	Remote Similarity	NPD5127	Approved
0.6562	Remote Similarity	NPD3617	Approved
0.6562	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD6336	Discontinued

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