NPASS Compound

Structure

NPC185530 OpenBabel07101719512D 34 38 0 0 1 0 0 0 0 0999 V2000 -3.7536 2.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3359 1.6407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4442 1.6293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9346 0.6226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 1.3271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 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 -4.3414 1.5361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9401 0.5181 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 2 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 4.3301 -2.5000 0.0000 C 0 0 1 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 -0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 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 -1.3578 1.2226 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2533 2.2171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5334 -0.3955 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 9 11 1 0 0 0 0 9 19 2 0 0 0 0 10 12 1 0 0 0 0 10 20 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 17 2 0 0 0 0 14 18 1 0 0 0 0 14 29 1 0 0 0 0 15 27 1 0 0 0 0 16 24 1 0 0 0 0 16 28 1 0 0 0 0 18 13 1 1 0 0 0 18 34 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 0 0 0 0 20 30 1 6 0 0 0 21 15 1 1 0 0 0 21 25 1 0 0 0 0 21 34 1 0 0 0 0 22 27 1 1 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 6 0 0 0 24 30 1 0 0 0 0 24 32 2 0 0 0 0 25 28 1 6 0 0 0 25 29 1 0 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 7 1 1 0 0 0 29 33 1 0 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	511.905
LogP:	5.904
LogD:	4.179
LogS:	-5.326
# Rotatable Bonds:	1
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.489
Synthetic Accessibility Score:	5.426
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.96
MDCK Permeability:	1.3707480320590548e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.862

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.965
Plasma Protein Binding (PPB):	86.0008773803711%
Volume Distribution (VD):	1.819
Pgp-substrate:	7.336098670959473%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.316
CYP2C19-inhibitor:	0.168
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.226
CYP2C9-substrate:	0.079
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.743

ADMET: Excretion

Clearance (CL):	11.89
Half-life (T1/2):	0.123

ADMET: Toxicity

hERG Blockers:	0.203
Human Hepatotoxicity (H-HT):	0.738
Drug-inuced Liver Injury (DILI):	0.059
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.961
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.255
Carcinogencity:	0.2
Eye Corrosion:	0.004
Eye Irritation:	0.015
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC185530

Natural Product ID:	NPC185530
*Common Name:**	RTMOFHUFRVKXGA-VTQJDCRPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	RTMOFHUFRVKXGA-VTQJDCRPSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-17(2)13-18-14-29(7,33)25-21(34-18)15-27(5)22-11-9-19-20(10-12-23(31)26(19,3)4)30(22,8)24(32)16-28(25,27)6/h9,13,18,20-23,25,31,33H,10-12,14-16H2,1-8H3/t18-,20+,21+,22-,23-,25-,27-,28+,29-,30-/m0/s1
SMILES:	CC(=C[C@H]1C[C@@](C)([C@H]2[C@@H](C[C@@]3(C)[C@@H]4CC=C5[C@@H](CC[C@@H](C5(C)C)O)[C@]4(C)C(=O)C[C@]23C)O1)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2022242
PubChem CID:	70696055
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003059] 11-oxosteroids

*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
NPO32449	eleaocarpus chinensis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22239601]

☑ 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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	IC50	>	10000.0	nM	PMID[554331]

☑ 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 NPC185530 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	205
0.1-0.2	1266
0.2-0.3	4310
0.3-0.4	9647
0.4-0.5	12016
0.5-0.6	6196
0.6-0.7	5696
0.7-0.8	3123
0.8-0.85	219
0.85-0.9	10
0.9-0.95	4
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC26478
0.9691	High Similarity	NPC60681
0.9592	High Similarity	NPC144459
0.9495	High Similarity	NPC177064
0.9375	High Similarity	NPC83709
0.9192	High Similarity	NPC75531
0.9192	High Similarity	NPC149124
0.9	High Similarity	NPC137657
0.8889	High Similarity	NPC474327
0.8586	High Similarity	NPC190554
0.8586	High Similarity	NPC291634
0.8586	High Similarity	NPC126815
0.8571	High Similarity	NPC469599
0.8571	High Similarity	NPC472932
0.8542	High Similarity	NPC320026
0.8515	High Similarity	NPC473174
0.85	High Similarity	NPC471784
0.85	High Similarity	NPC303777
0.8485	Intermediate Similarity	NPC160056
0.8462	Intermediate Similarity	NPC185
0.8438	Intermediate Similarity	NPC32830
0.8438	Intermediate Similarity	NPC474245
0.8438	Intermediate Similarity	NPC2983
0.8438	Intermediate Similarity	NPC76879
0.8438	Intermediate Similarity	NPC1015
0.8438	Intermediate Similarity	NPC31985
0.8431	Intermediate Similarity	NPC477915
0.8431	Intermediate Similarity	NPC473424
0.8431	Intermediate Similarity	NPC87351
0.8421	Intermediate Similarity	NPC317590
0.8416	Intermediate Similarity	NPC15390
0.8416	Intermediate Similarity	NPC473176
0.8411	Intermediate Similarity	NPC100267
0.8411	Intermediate Similarity	NPC475524
0.84	Intermediate Similarity	NPC18509
0.8367	Intermediate Similarity	NPC472930
0.8367	Intermediate Similarity	NPC472942
0.8365	Intermediate Similarity	NPC478052
0.8365	Intermediate Similarity	NPC231530
0.8365	Intermediate Similarity	NPC149047
0.8365	Intermediate Similarity	NPC278628
0.8364	Intermediate Similarity	NPC257457
0.8364	Intermediate Similarity	NPC311554
0.8351	Intermediate Similarity	NPC171441
0.8351	Intermediate Similarity	NPC48010
0.835	Intermediate Similarity	NPC311612
0.835	Intermediate Similarity	NPC191892
0.8333	Intermediate Similarity	NPC476897
0.8333	Intermediate Similarity	NPC328313
0.8333	Intermediate Similarity	NPC53911
0.8317	Intermediate Similarity	NPC477854
0.8316	Intermediate Similarity	NPC469994
0.8302	Intermediate Similarity	NPC214644
0.83	Intermediate Similarity	NPC249954
0.83	Intermediate Similarity	NPC78473
0.83	Intermediate Similarity	NPC49371
0.8298	Intermediate Similarity	NPC59453
0.8298	Intermediate Similarity	NPC221758
0.8298	Intermediate Similarity	NPC82902
0.8288	Intermediate Similarity	NPC475041
0.8286	Intermediate Similarity	NPC83744
0.8286	Intermediate Similarity	NPC475294
0.8286	Intermediate Similarity	NPC475060
0.8286	Intermediate Similarity	NPC220229
0.8286	Intermediate Similarity	NPC477916
0.8283	Intermediate Similarity	NPC292793
0.8273	Intermediate Similarity	NPC470959
0.8273	Intermediate Similarity	NPC476965
0.8269	Intermediate Similarity	NPC204833
0.8269	Intermediate Similarity	NPC209502
0.8265	Intermediate Similarity	NPC472975
0.8252	Intermediate Similarity	NPC473928
0.8252	Intermediate Similarity	NPC136289
0.8247	Intermediate Similarity	NPC477943
0.8241	Intermediate Similarity	NPC476163
0.8241	Intermediate Similarity	NPC221144
0.8241	Intermediate Similarity	NPC207251
0.8235	Intermediate Similarity	NPC154072
0.8235	Intermediate Similarity	NPC477521
0.8235	Intermediate Similarity	NPC110149
0.8235	Intermediate Similarity	NPC144956
0.8229	Intermediate Similarity	NPC475740
0.8229	Intermediate Similarity	NPC90652
0.8229	Intermediate Similarity	NPC149224
0.8224	Intermediate Similarity	NPC76084
0.8218	Intermediate Similarity	NPC107243
0.8218	Intermediate Similarity	NPC57416
0.8218	Intermediate Similarity	NPC151488
0.8218	Intermediate Similarity	NPC475894
0.8211	Intermediate Similarity	NPC266511
0.8211	Intermediate Similarity	NPC474218
0.8211	Intermediate Similarity	NPC471224
0.8208	Intermediate Similarity	NPC329417
0.8208	Intermediate Similarity	NPC217201
0.8208	Intermediate Similarity	NPC94529
0.82	Intermediate Similarity	NPC259286
0.82	Intermediate Similarity	NPC473170
0.8198	Intermediate Similarity	NPC329736
0.8191	Intermediate Similarity	NPC278648
0.8191	Intermediate Similarity	NPC476082
0.8191	Intermediate Similarity	NPC470047
0.8191	Intermediate Similarity	NPC470046
0.819	Intermediate Similarity	NPC48733
0.819	Intermediate Similarity	NPC296945
0.819	Intermediate Similarity	NPC260268
0.819	Intermediate Similarity	NPC50692
0.819	Intermediate Similarity	NPC202167
0.819	Intermediate Similarity	NPC49958
0.819	Intermediate Similarity	NPC476027
0.819	Intermediate Similarity	NPC152695
0.819	Intermediate Similarity	NPC319077
0.819	Intermediate Similarity	NPC171137
0.819	Intermediate Similarity	NPC214264
0.819	Intermediate Similarity	NPC85829
0.819	Intermediate Similarity	NPC257353
0.819	Intermediate Similarity	NPC150531
0.819	Intermediate Similarity	NPC302607
0.819	Intermediate Similarity	NPC97202
0.8182	Intermediate Similarity	NPC477520
0.8182	Intermediate Similarity	NPC148458
0.8182	Intermediate Similarity	NPC69454
0.8173	Intermediate Similarity	NPC112009
0.8173	Intermediate Similarity	NPC324001
0.8173	Intermediate Similarity	NPC236390
0.8173	Intermediate Similarity	NPC36688
0.8173	Intermediate Similarity	NPC111323
0.8165	Intermediate Similarity	NPC317210
0.8165	Intermediate Similarity	NPC122056
0.8163	Intermediate Similarity	NPC69622
0.8158	Intermediate Similarity	NPC473979
0.8158	Intermediate Similarity	NPC204812
0.8155	Intermediate Similarity	NPC81530
0.8148	Intermediate Similarity	NPC43775
0.8144	Intermediate Similarity	NPC470417
0.8144	Intermediate Similarity	NPC328539
0.8137	Intermediate Similarity	NPC197386
0.8137	Intermediate Similarity	NPC176845
0.8131	Intermediate Similarity	NPC11710
0.8131	Intermediate Similarity	NPC472216
0.8131	Intermediate Similarity	NPC284828
0.8131	Intermediate Similarity	NPC173905
0.8131	Intermediate Similarity	NPC5475
0.8125	Intermediate Similarity	NPC264954
0.8125	Intermediate Similarity	NPC31564
0.8125	Intermediate Similarity	NPC474778
0.8125	Intermediate Similarity	NPC476960
0.8125	Intermediate Similarity	NPC51014
0.8125	Intermediate Similarity	NPC474733
0.8125	Intermediate Similarity	NPC145879
0.8125	Intermediate Similarity	NPC470050
0.8125	Intermediate Similarity	NPC20688
0.8125	Intermediate Similarity	NPC473270
0.8125	Intermediate Similarity	NPC470051
0.8125	Intermediate Similarity	NPC61520
0.8125	Intermediate Similarity	NPC474732
0.8119	Intermediate Similarity	NPC328371
0.8119	Intermediate Similarity	NPC471463
0.8119	Intermediate Similarity	NPC173272
0.8119	Intermediate Similarity	NPC477853
0.8113	Intermediate Similarity	NPC165873
0.8113	Intermediate Similarity	NPC64844
0.8113	Intermediate Similarity	NPC44063
0.8113	Intermediate Similarity	NPC42847
0.8108	Intermediate Similarity	NPC239273
0.8108	Intermediate Similarity	NPC476959
0.8108	Intermediate Similarity	NPC471854
0.81	Intermediate Similarity	NPC8993
0.81	Intermediate Similarity	NPC174051
0.81	Intermediate Similarity	NPC67831
0.81	Intermediate Similarity	NPC111015
0.8095	Intermediate Similarity	NPC473175
0.8091	Intermediate Similarity	NPC147912
0.8091	Intermediate Similarity	NPC470953
0.8091	Intermediate Similarity	NPC67259
0.8091	Intermediate Similarity	NPC326542
0.8087	Intermediate Similarity	NPC32868
0.8087	Intermediate Similarity	NPC241456
0.8085	Intermediate Similarity	NPC151519
0.8081	Intermediate Similarity	NPC168027
0.8081	Intermediate Similarity	NPC63748
0.8081	Intermediate Similarity	NPC185936
0.8081	Intermediate Similarity	NPC472978
0.8081	Intermediate Similarity	NPC154101
0.8081	Intermediate Similarity	NPC262870
0.8081	Intermediate Similarity	NPC473998
0.8081	Intermediate Similarity	NPC475806
0.8077	Intermediate Similarity	NPC155332
0.8077	Intermediate Similarity	NPC195290
0.8077	Intermediate Similarity	NPC22388
0.8077	Intermediate Similarity	NPC32577
0.8077	Intermediate Similarity	NPC204450
0.8077	Intermediate Similarity	NPC114540
0.8073	Intermediate Similarity	NPC280782
0.8073	Intermediate Similarity	NPC126691
0.8073	Intermediate Similarity	NPC191620
0.807	Intermediate Similarity	NPC269642
0.8061	Intermediate Similarity	NPC275740
0.8061	Intermediate Similarity	NPC86319
0.8061	Intermediate Similarity	NPC472970
0.8061	Intermediate Similarity	NPC473999

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 NPC185530 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1482
0.2-0.3	3791
0.3-0.4	2468
0.4-0.5	718
0.5-0.6	177
0.6-0.7	174
0.7-0.8	147
0.8-0.85	23
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.84	Intermediate Similarity	NPD4755	Approved
0.8365	Intermediate Similarity	NPD5739	Approved
0.8365	Intermediate Similarity	NPD7128	Approved
0.8365	Intermediate Similarity	NPD6675	Approved
0.8365	Intermediate Similarity	NPD6402	Approved
0.8298	Intermediate Similarity	NPD4786	Approved
0.8252	Intermediate Similarity	NPD5211	Phase 2
0.8247	Intermediate Similarity	NPD5328	Approved
0.8235	Intermediate Similarity	NPD5285	Approved
0.8235	Intermediate Similarity	NPD4700	Approved
0.8235	Intermediate Similarity	NPD4696	Approved
0.8235	Intermediate Similarity	NPD5286	Approved
0.8208	Intermediate Similarity	NPD7320	Approved
0.8208	Intermediate Similarity	NPD6881	Approved
0.8208	Intermediate Similarity	NPD6899	Approved
0.8131	Intermediate Similarity	NPD6372	Approved
0.8131	Intermediate Similarity	NPD6373	Approved
0.8113	Intermediate Similarity	NPD5701	Approved
0.8113	Intermediate Similarity	NPD5697	Approved
0.8095	Intermediate Similarity	NPD5141	Approved
0.8085	Intermediate Similarity	NPD3667	Approved
0.8081	Intermediate Similarity	NPD6079	Approved
0.8077	Intermediate Similarity	NPD5226	Approved
0.8077	Intermediate Similarity	NPD5225	Approved
0.8077	Intermediate Similarity	NPD4633	Approved
0.8077	Intermediate Similarity	NPD5224	Approved
0.8061	Intermediate Similarity	NPD4753	Phase 2
0.8056	Intermediate Similarity	NPD6883	Approved
0.8056	Intermediate Similarity	NPD7102	Approved
0.8056	Intermediate Similarity	NPD7290	Approved
0.8039	Intermediate Similarity	NPD6084	Phase 2
0.8039	Intermediate Similarity	NPD6083	Phase 2
0.8	Intermediate Similarity	NPD5174	Approved
0.8	Intermediate Similarity	NPD5175	Approved
0.8	Intermediate Similarity	NPD4202	Approved
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7982	Intermediate Similarity	NPD6649	Approved
0.7982	Intermediate Similarity	NPD6617	Approved
0.7982	Intermediate Similarity	NPD8130	Phase 1
0.7982	Intermediate Similarity	NPD6847	Approved
0.7982	Intermediate Similarity	NPD6650	Approved
0.7982	Intermediate Similarity	NPD6869	Approved
0.7981	Intermediate Similarity	NPD5223	Approved
0.7963	Intermediate Similarity	NPD6014	Approved
0.7963	Intermediate Similarity	NPD6013	Approved
0.7963	Intermediate Similarity	NPD6012	Approved
0.7946	Intermediate Similarity	NPD7115	Discovery
0.7917	Intermediate Similarity	NPD3665	Phase 1
0.7917	Intermediate Similarity	NPD3666	Approved
0.7917	Intermediate Similarity	NPD3133	Approved
0.7909	Intermediate Similarity	NPD8297	Approved
0.7909	Intermediate Similarity	NPD6882	Approved
0.787	Intermediate Similarity	NPD6011	Approved
0.785	Intermediate Similarity	NPD4767	Approved
0.785	Intermediate Similarity	NPD4768	Approved
0.783	Intermediate Similarity	NPD4754	Approved
0.7818	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7788	Intermediate Similarity	NPD7638	Approved
0.7767	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD5222	Approved
0.7767	Intermediate Similarity	NPD4697	Phase 3
0.7767	Intermediate Similarity	NPD5221	Approved
0.7755	Intermediate Similarity	NPD3618	Phase 1
0.7714	Intermediate Similarity	NPD7640	Approved
0.7714	Intermediate Similarity	NPD7639	Approved
0.7712	Intermediate Similarity	NPD7507	Approved
0.7708	Intermediate Similarity	NPD4221	Approved
0.7708	Intermediate Similarity	NPD4223	Phase 3
0.7706	Intermediate Similarity	NPD4730	Approved
0.7706	Intermediate Similarity	NPD4729	Approved
0.7706	Intermediate Similarity	NPD5128	Approved
0.7692	Intermediate Similarity	NPD5173	Approved
0.767	Intermediate Similarity	NPD5210	Approved
0.767	Intermediate Similarity	NPD5695	Phase 3
0.767	Intermediate Similarity	NPD4629	Approved
0.7653	Intermediate Similarity	NPD5329	Approved
0.7619	Intermediate Similarity	NPD5696	Approved
0.7615	Intermediate Similarity	NPD6412	Phase 2
0.76	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD6053	Discontinued
0.7576	Intermediate Similarity	NPD7146	Approved
0.7576	Intermediate Similarity	NPD7334	Approved
0.7576	Intermediate Similarity	NPD5330	Approved
0.7576	Intermediate Similarity	NPD7521	Approved
0.7576	Intermediate Similarity	NPD6409	Approved
0.7576	Intermediate Similarity	NPD6684	Approved
0.7568	Intermediate Similarity	NPD5251	Approved
0.7568	Intermediate Similarity	NPD5247	Approved
0.7568	Intermediate Similarity	NPD4634	Approved
0.7568	Intermediate Similarity	NPD5249	Phase 3
0.7568	Intermediate Similarity	NPD5250	Approved
0.7568	Intermediate Similarity	NPD5248	Approved
0.7551	Intermediate Similarity	NPD4197	Approved
0.7551	Intermediate Similarity	NPD3668	Phase 3
0.7549	Intermediate Similarity	NPD5693	Phase 1
0.7544	Intermediate Similarity	NPD6274	Approved
0.7525	Intermediate Similarity	NPD6051	Approved
0.7523	Intermediate Similarity	NPD6008	Approved
0.7521	Intermediate Similarity	NPD7319	Approved
0.75	Intermediate Similarity	NPD5215	Approved
0.75	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD7101	Approved
0.75	Intermediate Similarity	NPD5217	Approved
0.75	Intermediate Similarity	NPD5216	Approved
0.7449	Intermediate Similarity	NPD4788	Approved
0.7447	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD6054	Approved
0.7436	Intermediate Similarity	NPD6059	Approved
0.7426	Intermediate Similarity	NPD6903	Approved
0.7414	Intermediate Similarity	NPD6335	Approved
0.7411	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD5169	Approved
0.7411	Intermediate Similarity	NPD5135	Approved
0.7404	Intermediate Similarity	NPD7748	Approved
0.74	Intermediate Similarity	NPD6098	Approved
0.74	Intermediate Similarity	NPD4693	Phase 3
0.74	Intermediate Similarity	NPD4690	Approved
0.74	Intermediate Similarity	NPD4689	Approved
0.74	Intermediate Similarity	NPD4688	Approved
0.74	Intermediate Similarity	NPD4138	Approved
0.74	Intermediate Similarity	NPD5205	Approved
0.7379	Intermediate Similarity	NPD7515	Phase 2
0.7373	Intermediate Similarity	NPD6908	Approved
0.7373	Intermediate Similarity	NPD6909	Approved
0.7368	Intermediate Similarity	NPD4632	Approved
0.7353	Intermediate Similarity	NPD6904	Approved
0.7353	Intermediate Similarity	NPD6080	Approved
0.7353	Intermediate Similarity	NPD6673	Approved
0.7345	Intermediate Similarity	NPD5127	Approved
0.734	Intermediate Similarity	NPD7339	Approved
0.734	Intermediate Similarity	NPD6942	Approved
0.7333	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD6317	Approved
0.7327	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7525	Registered
0.7311	Intermediate Similarity	NPD6370	Approved
0.73	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD6319	Approved
0.7265	Intermediate Similarity	NPD6313	Approved
0.7265	Intermediate Similarity	NPD6314	Approved
0.7255	Intermediate Similarity	NPD6672	Approved
0.7255	Intermediate Similarity	NPD5737	Approved
0.7228	Intermediate Similarity	NPD5690	Phase 2
0.7228	Intermediate Similarity	NPD5279	Phase 3
0.7228	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD4694	Approved
0.7228	Intermediate Similarity	NPD5280	Approved
0.7227	Intermediate Similarity	NPD6016	Approved
0.7227	Intermediate Similarity	NPD6015	Approved
0.7212	Intermediate Similarity	NPD8034	Phase 2
0.7212	Intermediate Similarity	NPD6411	Approved
0.7212	Intermediate Similarity	NPD8035	Phase 2
0.7196	Intermediate Similarity	NPD7902	Approved
0.719	Intermediate Similarity	NPD7492	Approved
0.7179	Intermediate Similarity	NPD6009	Approved
0.7167	Intermediate Similarity	NPD5988	Approved
0.7157	Intermediate Similarity	NPD3573	Approved
0.7155	Intermediate Similarity	NPD5167	Approved
0.7154	Intermediate Similarity	NPD7736	Approved
0.7131	Intermediate Similarity	NPD6616	Approved
0.7119	Intermediate Similarity	NPD7328	Approved
0.7119	Intermediate Similarity	NPD7327	Approved
0.7107	Intermediate Similarity	NPD7604	Phase 2
0.71	Intermediate Similarity	NPD6695	Phase 3
0.7094	Intermediate Similarity	NPD6868	Approved
0.7091	Intermediate Similarity	NPD7632	Discontinued
0.7087	Intermediate Similarity	NPD5208	Approved
0.7083	Intermediate Similarity	NPD5983	Phase 2
0.7083	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8033	Approved
0.708	Intermediate Similarity	NPD5168	Approved
0.7073	Intermediate Similarity	NPD8293	Discontinued
0.7073	Intermediate Similarity	NPD7078	Approved
0.7071	Intermediate Similarity	NPD4692	Approved
0.7071	Intermediate Similarity	NPD4139	Approved
0.7059	Intermediate Similarity	NPD7516	Approved
0.7053	Intermediate Similarity	NPD4785	Approved
0.7053	Intermediate Similarity	NPD4784	Approved
0.7048	Intermediate Similarity	NPD5284	Approved
0.7048	Intermediate Similarity	NPD5281	Approved
0.7048	Intermediate Similarity	NPD6050	Approved
0.7041	Intermediate Similarity	NPD4195	Approved
0.7041	Intermediate Similarity	NPD7645	Phase 2
0.703	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4243	Approved
0.7019	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6101	Approved
0.7	Intermediate Similarity	NPD8377	Approved
0.7	Intermediate Similarity	NPD8294	Approved
0.7	Intermediate Similarity	NPD6435	Approved
0.6992	Remote Similarity	NPD6336	Discontinued
0.6972	Remote Similarity	NPD4225	Approved
0.6952	Remote Similarity	NPD5785	Approved
0.6952	Remote Similarity	NPD5692	Phase 3
0.6942	Remote Similarity	NPD7503	Approved
0.6942	Remote Similarity	NPD8378	Approved
0.6942	Remote Similarity	NPD8335	Approved
0.6942	Remote Similarity	NPD8379	Approved
0.6942	Remote Similarity	NPD8380	Approved
0.6942	Remote Similarity	NPD8296	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