NPASS Compound

Structure

NPC470590 OpenBabel07101719252D 36 40 0 0 1 0 0 0 0 0999 V2000 5.9143 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1776 3.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2020 3.7717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8674 -2.7961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8918 -2.7961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6898 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2245 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5347 1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -0.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 2.4390 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9143 -1.4634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5347 -1.4634 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.6898 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2245 -1.4634 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 2.9268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3796 -1.9512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6898 0.9756 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5347 -0.4878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8449 -0.4878 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 6.7592 -1.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8449 -2.4390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8449 -2.4390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0694 -1.9512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 8 31 1 0 0 0 0 9 10 1 0 0 0 0 9 21 2 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 30 1 0 0 0 0 14 31 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 29 1 0 0 0 0 17 18 1 0 0 0 0 17 29 1 0 0 0 0 18 32 1 0 0 0 0 19 22 1 0 0 0 0 19 27 1 0 0 0 0 20 33 2 0 0 0 0 20 36 1 0 0 0 0 21 22 1 0 0 0 0 21 32 1 0 0 0 0 22 29 1 1 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 30 1 6 0 0 0 24 31 1 0 0 0 0 25 28 1 0 0 0 0 25 36 1 6 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 29 6 1 6 0 0 0 30 7 1 6 0 0 0 31 32 1 1 0 0 0 32 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.37
Volume:	546.497
LogP:	6.664
LogD:	5.137
LogS:	-5.548
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.311
Synthetic Accessibility Score:	4.745
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.175
MDCK Permeability:	2.6565110601950437e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.07
30% Bioavailability (F30%):	0.656

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	96.62174987792969%
Volume Distribution (VD):	0.812
Pgp-substrate:	2.624027729034424%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.154
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.18
CYP2C9-substrate:	0.929
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.233
CYP3A4-inhibitor:	0.191
CYP3A4-substrate:	0.318

ADMET: Excretion

Clearance (CL):	2.018
Half-life (T1/2):	0.047

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.137
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.575
Skin Sensitization:	0.249
Carcinogencity:	0.015
Eye Corrosion:	0.118
Eye Irritation:	0.468
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC470590

Natural Product ID:	NPC470590
*Common Name:**	3Beta-Acetoxyolean-12-En-27-Oic Acid
IUPAC Name:	(4aR,6aR,6aR,6bR,10S,12aR,14bR)-10-acetyloxy-2,2,4a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-6a-carboxylic acid
Synonyms:
Standard InCHIKey:	IQYUEJTVDLHZDJ-PVLVPSCMSA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-20(33)36-25-12-13-30(7)23(28(25,4)5)11-14-31(8)24(30)10-9-21-22-19-27(2,3)15-16-29(22,6)17-18-32(21,31)26(34)35/h9,22-25H,10-19H2,1-8H3,(H,34,35)/t22-,23?,24+,25-,29+,30-,31+,32+/m0/s1
SMILES:	CC(=O)O[C@H]1CC[C@]2(C(C1(C)C)CC[C@@]1([C@@H]2CC=C2[C@]1(CC[C@@]1([C@H]2CC(C)(C)CC1)C)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL208639
PubChem CID:	44411975
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
NPO21023	Astilbe koreana	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16580200]
NPO21023	Astilbe koreana	Species	Saxifragaceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	8500.0	nM	PMID[528381]

☑ 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 NPC470590 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	1291
0.2-0.3	4616
0.3-0.4	13209
0.4-0.5	9792
0.5-0.6	5687
0.6-0.7	5005
0.7-0.8	2103
0.8-0.85	441
0.85-0.9	146
0.9-0.95	169
0.95-1	30

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC285184
1.0	High Similarity	NPC77099
1.0	High Similarity	NPC60755
0.9882	High Similarity	NPC120840
0.9882	High Similarity	NPC474728
0.9882	High Similarity	NPC113989
0.9765	High Similarity	NPC30522
0.9659	High Similarity	NPC195715
0.9655	High Similarity	NPC86368
0.9551	High Similarity	NPC327179
0.9545	High Similarity	NPC296164
0.9545	High Similarity	NPC78580
0.9545	High Similarity	NPC23621
0.9545	High Similarity	NPC184006
0.9545	High Similarity	NPC74751
0.9535	High Similarity	NPC274330
0.9535	High Similarity	NPC470588
0.9535	High Similarity	NPC143232
0.9535	High Similarity	NPC198664
0.9529	High Similarity	NPC46912
0.9529	High Similarity	NPC162107
0.9444	High Similarity	NPC158347
0.9438	High Similarity	NPC474727
0.9438	High Similarity	NPC23241
0.9425	High Similarity	NPC470589
0.9425	High Similarity	NPC111110
0.9425	High Similarity	NPC126369
0.9419	High Similarity	NPC246708
0.9419	High Similarity	NPC470629
0.9419	High Similarity	NPC290690
0.9419	High Similarity	NPC182797
0.9419	High Similarity	NPC17733
0.9419	High Similarity	NPC40552
0.9419	High Similarity	NPC474512
0.9419	High Similarity	NPC181225
0.9419	High Similarity	NPC473242
0.9419	High Similarity	NPC52169
0.9412	High Similarity	NPC91525
0.9412	High Similarity	NPC10005
0.9412	High Similarity	NPC329943
0.9412	High Similarity	NPC9892
0.9341	High Similarity	NPC58942
0.9341	High Similarity	NPC260149
0.9333	High Similarity	NPC230151
0.9318	High Similarity	NPC187722
0.931	High Similarity	NPC25906
0.931	High Similarity	NPC225585
0.931	High Similarity	NPC64872
0.931	High Similarity	NPC130520
0.931	High Similarity	NPC121798
0.931	High Similarity	NPC127689
0.931	High Similarity	NPC234346
0.931	High Similarity	NPC59263
0.931	High Similarity	NPC270768
0.931	High Similarity	NPC293048
0.931	High Similarity	NPC263393
0.931	High Similarity	NPC61543
0.931	High Similarity	NPC475049
0.931	High Similarity	NPC290972
0.9302	High Similarity	NPC242468
0.9302	High Similarity	NPC171203
0.9302	High Similarity	NPC18064
0.9302	High Similarity	NPC68160
0.9302	High Similarity	NPC293564
0.9302	High Similarity	NPC98442
0.9302	High Similarity	NPC88716
0.9302	High Similarity	NPC142415
0.9302	High Similarity	NPC130577
0.9302	High Similarity	NPC102683
0.9302	High Similarity	NPC51700
0.9302	High Similarity	NPC307426
0.9231	High Similarity	NPC476878
0.9231	High Similarity	NPC476879
0.9231	High Similarity	NPC26413
0.9213	High Similarity	NPC49776
0.9213	High Similarity	NPC214756
0.9213	High Similarity	NPC158059
0.9213	High Similarity	NPC74855
0.9213	High Similarity	NPC307335
0.9213	High Similarity	NPC229281
0.9213	High Similarity	NPC295643
0.9213	High Similarity	NPC136313
0.9213	High Similarity	NPC63118
0.9213	High Similarity	NPC474436
0.9213	High Similarity	NPC118519
0.9213	High Similarity	NPC202728
0.9213	High Similarity	NPC272075
0.9205	High Similarity	NPC120968
0.9205	High Similarity	NPC477872
0.9205	High Similarity	NPC7260
0.9205	High Similarity	NPC227467
0.9205	High Similarity	NPC18872
0.9205	High Similarity	NPC273621
0.9205	High Similarity	NPC290614
0.9205	High Similarity	NPC291028
0.9205	High Similarity	NPC130278
0.9205	High Similarity	NPC210037
0.9195	High Similarity	NPC224145
0.9186	High Similarity	NPC72638
0.9186	High Similarity	NPC325594
0.914	High Similarity	NPC233012
0.914	High Similarity	NPC54909
0.913	High Similarity	NPC471966
0.9111	High Similarity	NPC209868
0.9111	High Similarity	NPC159365
0.9111	High Similarity	NPC114159
0.9111	High Similarity	NPC191412
0.9111	High Similarity	NPC6818
0.9111	High Similarity	NPC91010
0.9101	High Similarity	NPC228784
0.9101	High Similarity	NPC38754
0.9101	High Similarity	NPC233455
0.9101	High Similarity	NPC472149
0.9101	High Similarity	NPC25299
0.9101	High Similarity	NPC282616
0.9101	High Similarity	NPC52021
0.9101	High Similarity	NPC84319
0.9101	High Similarity	NPC145067
0.9101	High Similarity	NPC306541
0.9101	High Similarity	NPC4036
0.9101	High Similarity	NPC65120
0.9101	High Similarity	NPC288833
0.9101	High Similarity	NPC474525
0.9101	High Similarity	NPC158030
0.9101	High Similarity	NPC235884
0.9101	High Similarity	NPC324341
0.9101	High Similarity	NPC71074
0.9101	High Similarity	NPC300351
0.9101	High Similarity	NPC155120
0.9101	High Similarity	NPC105189
0.9101	High Similarity	NPC966
0.9091	High Similarity	NPC474700
0.9091	High Similarity	NPC474972
0.9091	High Similarity	NPC95246
0.9091	High Similarity	NPC474686
0.9091	High Similarity	NPC161751
0.908	High Similarity	NPC71507
0.907	High Similarity	NPC191965
0.9059	High Similarity	NPC200752
0.9059	High Similarity	NPC132386
0.9022	High Similarity	NPC255589
0.9022	High Similarity	NPC259788
0.9011	High Similarity	NPC96916
0.9011	High Similarity	NPC473240
0.9	High Similarity	NPC275809
0.9	High Similarity	NPC474806
0.9	High Similarity	NPC169343
0.9	High Similarity	NPC298554
0.9	High Similarity	NPC133579
0.8989	High Similarity	NPC471896
0.8989	High Similarity	NPC86372
0.8989	High Similarity	NPC46441
0.8989	High Similarity	NPC172361
0.8989	High Similarity	NPC49320
0.8989	High Similarity	NPC193750
0.8966	High Similarity	NPC73038
0.8966	High Similarity	NPC137306
0.8966	High Similarity	NPC84121
0.8953	High Similarity	NPC312660
0.8941	High Similarity	NPC286786
0.8925	High Similarity	NPC475876
0.8925	High Similarity	NPC164349
0.8913	High Similarity	NPC132824
0.8913	High Similarity	NPC259733
0.8913	High Similarity	NPC173744
0.8913	High Similarity	NPC158371
0.8913	High Similarity	NPC98874
0.8913	High Similarity	NPC62516
0.8913	High Similarity	NPC73004
0.8913	High Similarity	NPC476327
0.8913	High Similarity	NPC157113
0.8913	High Similarity	NPC116457
0.8913	High Similarity	NPC476318
0.8913	High Similarity	NPC207922
0.8913	High Similarity	NPC204961
0.8901	High Similarity	NPC80365
0.8901	High Similarity	NPC474529
0.8901	High Similarity	NPC32407
0.8901	High Similarity	NPC88116
0.8901	High Similarity	NPC231063
0.8901	High Similarity	NPC222047
0.8901	High Similarity	NPC263548
0.8901	High Similarity	NPC87095
0.8901	High Similarity	NPC20235
0.8901	High Similarity	NPC299996
0.8901	High Similarity	NPC474963
0.8901	High Similarity	NPC145667
0.8901	High Similarity	NPC282395
0.8889	High Similarity	NPC26888
0.8889	High Similarity	NPC301244
0.8889	High Similarity	NPC471588
0.8889	High Similarity	NPC6255
0.8889	High Similarity	NPC475708
0.8864	High Similarity	NPC73064
0.8851	High Similarity	NPC133954
0.883	High Similarity	NPC475156
0.883	High Similarity	NPC473576
0.8824	High Similarity	NPC108476
0.8824	High Similarity	NPC290495
0.8824	High Similarity	NPC195334

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 NPC470590 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1580
0.2-0.3	3773
0.3-0.4	2367
0.4-0.5	762
0.5-0.6	224
0.6-0.7	203
0.7-0.8	47
0.8-0.85	3
0.85-0.9	2
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9545	High Similarity	NPD7748	Approved
0.9231	High Similarity	NPD7902	Approved
0.9101	High Similarity	NPD7515	Phase 2
0.8901	High Similarity	NPD7901	Clinical (unspecified phase)
0.8901	High Similarity	NPD7900	Approved
0.8478	Intermediate Similarity	NPD8035	Phase 2
0.8478	Intermediate Similarity	NPD8034	Phase 2
0.8387	Intermediate Similarity	NPD6399	Phase 3
0.8222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD7645	Phase 2
0.7957	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD4786	Approved
0.7889	Intermediate Similarity	NPD3667	Approved
0.7872	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7638	Approved
0.7742	Intermediate Similarity	NPD3618	Phase 1
0.7742	Intermediate Similarity	NPD6684	Approved
0.7742	Intermediate Similarity	NPD7334	Approved
0.7742	Intermediate Similarity	NPD7521	Approved
0.7742	Intermediate Similarity	NPD6409	Approved
0.7742	Intermediate Similarity	NPD7146	Approved
0.7742	Intermediate Similarity	NPD5330	Approved
0.7708	Intermediate Similarity	NPD6411	Approved
0.77	Intermediate Similarity	NPD7640	Approved
0.77	Intermediate Similarity	NPD7639	Approved
0.7684	Intermediate Similarity	NPD5328	Approved
0.767	Intermediate Similarity	NPD7128	Approved
0.767	Intermediate Similarity	NPD6402	Approved
0.767	Intermediate Similarity	NPD5739	Approved
0.767	Intermediate Similarity	NPD6675	Approved
0.766	Intermediate Similarity	NPD3573	Approved
0.7579	Intermediate Similarity	NPD5737	Approved
0.7579	Intermediate Similarity	NPD6672	Approved
0.7579	Intermediate Similarity	NPD6903	Approved
0.7527	Intermediate Similarity	NPD3668	Phase 3
0.7526	Intermediate Similarity	NPD6079	Approved
0.7524	Intermediate Similarity	NPD6899	Approved
0.7524	Intermediate Similarity	NPD6881	Approved
0.7524	Intermediate Similarity	NPD7320	Approved
0.75	Intermediate Similarity	NPD6083	Phase 2
0.75	Intermediate Similarity	NPD6101	Approved
0.75	Intermediate Similarity	NPD6084	Phase 2
0.75	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD8130	Phase 1
0.7455	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6373	Approved
0.7453	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6372	Approved
0.7429	Intermediate Similarity	NPD5697	Approved
0.7429	Intermediate Similarity	NPD5701	Approved
0.7407	Intermediate Similarity	NPD8297	Approved
0.7383	Intermediate Similarity	NPD7290	Approved
0.7383	Intermediate Similarity	NPD6883	Approved
0.7383	Intermediate Similarity	NPD7102	Approved
0.7368	Intermediate Similarity	NPD8328	Phase 3
0.7358	Intermediate Similarity	NPD6011	Approved
0.734	Intermediate Similarity	NPD3665	Phase 1
0.734	Intermediate Similarity	NPD3666	Approved
0.734	Intermediate Similarity	NPD3133	Approved
0.7315	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6649	Approved
0.7315	Intermediate Similarity	NPD6869	Approved
0.7315	Intermediate Similarity	NPD6650	Approved
0.7315	Intermediate Similarity	NPD6847	Approved
0.7315	Intermediate Similarity	NPD6617	Approved
0.73	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD5695	Phase 3
0.7297	Intermediate Similarity	NPD7115	Discovery
0.729	Intermediate Similarity	NPD6014	Approved
0.729	Intermediate Similarity	NPD6012	Approved
0.729	Intermediate Similarity	NPD6013	Approved
0.7283	Intermediate Similarity	NPD7525	Registered
0.7283	Intermediate Similarity	NPD4695	Discontinued
0.7273	Intermediate Similarity	NPD4202	Approved
0.7255	Intermediate Similarity	NPD5696	Approved
0.7248	Intermediate Similarity	NPD6882	Approved
0.7228	Intermediate Similarity	NPD7614	Phase 1
0.7228	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4697	Phase 3
0.7228	Intermediate Similarity	NPD5222	Approved
0.7228	Intermediate Similarity	NPD5221	Approved
0.7228	Intermediate Similarity	NPD7732	Phase 3
0.7222	Intermediate Similarity	NPD6117	Approved
0.7188	Intermediate Similarity	NPD6098	Approved
0.717	Intermediate Similarity	NPD6008	Approved
0.7157	Intermediate Similarity	NPD5173	Approved
0.7157	Intermediate Similarity	NPD4755	Approved
0.7143	Intermediate Similarity	NPD6673	Approved
0.7143	Intermediate Similarity	NPD6116	Phase 1
0.7143	Intermediate Similarity	NPD6904	Approved
0.7143	Intermediate Similarity	NPD6080	Approved
0.7128	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD7339	Approved
0.7111	Intermediate Similarity	NPD6942	Approved
0.71	Intermediate Similarity	NPD5779	Approved
0.71	Intermediate Similarity	NPD5778	Approved
0.7087	Intermediate Similarity	NPD4225	Approved
0.7065	Intermediate Similarity	NPD6115	Approved
0.7065	Intermediate Similarity	NPD6697	Approved
0.7065	Intermediate Similarity	NPD6118	Approved
0.7065	Intermediate Similarity	NPD6114	Approved
0.7054	Intermediate Similarity	NPD6868	Approved
0.7048	Intermediate Similarity	NPD7632	Discontinued
0.7033	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5286	Approved
0.7019	Intermediate Similarity	NPD4700	Approved
0.7019	Intermediate Similarity	NPD4696	Approved
0.7019	Intermediate Similarity	NPD5285	Approved
0.701	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4753	Phase 2
0.6952	Remote Similarity	NPD5223	Approved
0.6947	Remote Similarity	NPD4223	Phase 3
0.6947	Remote Similarity	NPD4221	Approved
0.6944	Remote Similarity	NPD6412	Phase 2
0.693	Remote Similarity	NPD6335	Approved
0.6907	Remote Similarity	NPD5329	Approved
0.6907	Remote Similarity	NPD1694	Approved
0.6903	Remote Similarity	NPD6274	Approved
0.6887	Remote Similarity	NPD5211	Phase 2
0.6887	Remote Similarity	NPD5225	Approved
0.6887	Remote Similarity	NPD5226	Approved
0.6887	Remote Similarity	NPD5224	Approved
0.6887	Remote Similarity	NPD4633	Approved
0.6875	Remote Similarity	NPD8133	Approved
0.6875	Remote Similarity	NPD4632	Approved
0.687	Remote Similarity	NPD7101	Approved
0.687	Remote Similarity	NPD7100	Approved
0.6869	Remote Similarity	NPD5208	Approved
0.6863	Remote Similarity	NPD6001	Approved
0.6842	Remote Similarity	NPD6317	Approved
0.6837	Remote Similarity	NPD5279	Phase 3
0.6833	Remote Similarity	NPD7736	Approved
0.6832	Remote Similarity	NPD5693	Phase 1
0.6832	Remote Similarity	NPD6050	Approved
0.6832	Remote Similarity	NPD5281	Approved
0.6832	Remote Similarity	NPD5284	Approved
0.6822	Remote Similarity	NPD4754	Approved
0.6822	Remote Similarity	NPD5174	Approved
0.6822	Remote Similarity	NPD5175	Approved
0.6818	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4197	Approved
0.68	Remote Similarity	NPD6051	Approved
0.6783	Remote Similarity	NPD6314	Approved
0.6783	Remote Similarity	NPD6313	Approved
0.6759	Remote Similarity	NPD5141	Approved
0.6757	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6909	Approved
0.6752	Remote Similarity	NPD6908	Approved
0.6739	Remote Similarity	NPD8039	Approved
0.6737	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5692	Phase 3
0.6727	Remote Similarity	NPD6686	Approved
0.6702	Remote Similarity	NPD3617	Approved
0.6701	Remote Similarity	NPD4788	Approved
0.6697	Remote Similarity	NPD4767	Approved
0.6697	Remote Similarity	NPD4768	Approved
0.6696	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD4690	Approved
0.6667	Remote Similarity	NPD4689	Approved
0.6667	Remote Similarity	NPD5205	Approved
0.6667	Remote Similarity	NPD6422	Discontinued
0.6667	Remote Similarity	NPD4688	Approved
0.6667	Remote Similarity	NPD4138	Approved
0.6667	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD5694	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD4693	Phase 3
0.6667	Remote Similarity	NPD7637	Suspended
0.6667	Remote Similarity	NPD7507	Approved
0.6639	Remote Similarity	NPD7604	Phase 2
0.6635	Remote Similarity	NPD4629	Approved
0.6635	Remote Similarity	NPD5210	Approved
0.6612	Remote Similarity	NPD8293	Discontinued
0.661	Remote Similarity	NPD8033	Approved
0.661	Remote Similarity	NPD5983	Phase 2
0.661	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5777	Approved
0.6593	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD7492	Approved
0.6577	Remote Similarity	NPD5168	Approved
0.6577	Remote Similarity	NPD4729	Approved
0.6577	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD4730	Approved
0.6577	Remote Similarity	NPD5128	Approved
0.6569	Remote Similarity	NPD5207	Approved
0.6559	Remote Similarity	NPD8264	Approved
0.6556	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD7154	Phase 3
0.6531	Remote Similarity	NPD5362	Discontinued
0.6529	Remote Similarity	NPD6336	Discontinued
0.6529	Remote Similarity	NPD6616	Approved
0.6526	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD8377	Approved
0.6525	Remote Similarity	NPD6059	Approved
0.6525	Remote Similarity	NPD6054	Approved
0.6525	Remote Similarity	NPD8294	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