NPASS Compound

Structure

NPC67872 OpenBabel07101718192D 34 38 0 0 1 0 0 0 0 0999 V2000 -3.2500 5.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8973 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 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 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6102 4.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 3.0032 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 -3.9192 5.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9921 2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9703 2.4680 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6320 3.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6394 1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 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 7 8 1 0 0 0 0 7 22 1 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 9 20 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 13 14 1 0 0 0 0 13 27 1 0 0 0 0 15 18 2 0 0 0 0 15 21 1 0 0 0 0 16 31 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 19 16 1 1 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 27 1 6 0 0 0 21 25 1 0 0 0 0 21 32 1 1 0 0 0 22 26 1 0 0 0 0 22 29 1 6 0 0 0 23 28 1 1 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 33 1 6 0 0 0 25 34 1 6 0 0 0 27 28 1 6 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 14 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.37
Volume:	517.178
LogP:	4.863
LogD:	4.164
LogS:	-3.986
# Rotatable Bonds:	5
TPSA:	80.92
# H-Bond Aceptor:	4
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.419
Synthetic Accessibility Score:	5.929
Fsp3:	0.933
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:	-5.072
MDCK Permeability:	7.380339411611203e-06
Pgp-inhibitor:	0.245
Pgp-substrate:	0.05
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.966
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	88.22083282470703%
Volume Distribution (VD):	0.917
Pgp-substrate:	2.2703418731689453%

ADMET: Metabolism

CYP1A2-inhibitor:	0.017
CYP1A2-substrate:	0.233
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.862
CYP2C9-inhibitor:	0.062
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.074
CYP3A4-inhibitor:	0.746
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	6.924
Half-life (T1/2):	0.179

ADMET: Toxicity

hERG Blockers:	0.06
Human Hepatotoxicity (H-HT):	0.48
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.793
Maximum Recommended Daily Dose:	0.896
Skin Sensitization:	0.777
Carcinogencity:	0.074
Eye Corrosion:	0.005
Eye Irritation:	0.035
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC67872

Natural Product ID:	NPC67872
*Common Name:**	Argenteanol
IUPAC Name:	n.a.
Synonyms:	Argenteanol
Standard InCHIKey:	YAPWNPLDLBUZDW-XECJJSHOSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-18(2)15-21(32)25(34)19(16-31)20-9-11-28(6)23-8-7-22-26(3,4)24(33)10-12-29(22)17-30(23,29)14-13-27(20,28)5/h15,19-25,31-34H,7-14,16-17H2,1-6H3/t19-,20+,21-,22-,23-,24-,25-,27+,28-,29+,30-/m0/s1
SMILES:	OC[C@@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)O)C)[C@@H]([C@H](C=C(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2331819
PubChem CID:	71716958
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	leaves, twigs, and fruits	Nui Chua National Park (11 43' N; 109 08' E; 730 m alt.), Ninh Thuan Province, Vietnam	2010-Jan	PMID[23301897]
NPO4720	Aglaia perviridis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31621322]
NPO4720	Aglaia perviridis	Species	Meliaceae	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
ED50	2

Activity Type	# Activity
Cell Line	1
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	uM	PMID[481402]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	ED50	>	20.0	uM	PMID[481402]

☑ 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 NPC67872 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	184
0.1-0.2	1506
0.2-0.3	5392
0.3-0.4	14865
0.4-0.5	8746
0.5-0.6	5462
0.6-0.7	4963
0.7-0.8	1379
0.8-0.85	147
0.85-0.9	47
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9277	High Similarity	NPC185568
0.9176	High Similarity	NPC470620
0.9036	High Similarity	NPC101462
0.8977	High Similarity	NPC41554
0.8977	High Similarity	NPC275671
0.8977	High Similarity	NPC97404
0.8966	High Similarity	NPC470361
0.8929	High Similarity	NPC207013
0.8929	High Similarity	NPC317458
0.8929	High Similarity	NPC82623
0.8929	High Similarity	NPC474634
0.8876	High Similarity	NPC307776
0.8864	High Similarity	NPC3345
0.8864	High Similarity	NPC329596
0.8864	High Similarity	NPC80561
0.8864	High Similarity	NPC11216
0.8864	High Similarity	NPC291484
0.8864	High Similarity	NPC204188
0.8851	High Similarity	NPC474668
0.8837	High Similarity	NPC71520
0.8837	High Similarity	NPC6391
0.8837	High Similarity	NPC269058
0.8824	High Similarity	NPC205845
0.881	High Similarity	NPC30166
0.881	High Similarity	NPC218616
0.881	High Similarity	NPC296701
0.8795	High Similarity	NPC102253
0.8795	High Similarity	NPC236237
0.8795	High Similarity	NPC13554
0.8795	High Similarity	NPC322313
0.878	High Similarity	NPC65897
0.878	High Similarity	NPC167037
0.878	High Similarity	NPC302041
0.878	High Similarity	NPC244385
0.878	High Similarity	NPC138621
0.878	High Similarity	NPC6978
0.878	High Similarity	NPC85346
0.8721	High Similarity	NPC266511
0.8706	High Similarity	NPC113978
0.8706	High Similarity	NPC134481
0.8696	High Similarity	NPC476893
0.869	High Similarity	NPC474531
0.8675	High Similarity	NPC30986
0.8675	High Similarity	NPC209430
0.8675	High Similarity	NPC28862
0.8675	High Similarity	NPC47982
0.8675	High Similarity	NPC143182
0.8675	High Similarity	NPC84694
0.8675	High Similarity	NPC273410
0.8675	High Similarity	NPC81306
0.8675	High Similarity	NPC80530
0.8675	High Similarity	NPC109546
0.8659	High Similarity	NPC331618
0.8659	High Similarity	NPC257191
0.8636	High Similarity	NPC133588
0.8636	High Similarity	NPC475664
0.8621	High Similarity	NPC139724
0.8621	High Similarity	NPC261266
0.8621	High Similarity	NPC94462
0.8617	High Similarity	NPC476896
0.8602	High Similarity	NPC476895
0.8588	High Similarity	NPC49964
0.8587	High Similarity	NPC288970
0.8571	High Similarity	NPC234193
0.8571	High Similarity	NPC476186
0.8571	High Similarity	NPC236112
0.8554	High Similarity	NPC474216
0.8554	High Similarity	NPC472342
0.8554	High Similarity	NPC285761
0.8554	High Similarity	NPC312328
0.8554	High Similarity	NPC301707
0.8539	High Similarity	NPC105495
0.8539	High Similarity	NPC477606
0.8537	High Similarity	NPC237460
0.8523	High Similarity	NPC186145
0.8523	High Similarity	NPC474657
0.8523	High Similarity	NPC149224
0.8488	Intermediate Similarity	NPC475789
0.8488	Intermediate Similarity	NPC110778
0.8478	Intermediate Similarity	NPC476894
0.8471	Intermediate Similarity	NPC157655
0.8471	Intermediate Similarity	NPC209620
0.8471	Intermediate Similarity	NPC264245
0.8471	Intermediate Similarity	NPC23852
0.8462	Intermediate Similarity	NPC310013
0.8462	Intermediate Similarity	NPC476304
0.8452	Intermediate Similarity	NPC328714
0.8444	Intermediate Similarity	NPC473956
0.8444	Intermediate Similarity	NPC475751
0.8434	Intermediate Similarity	NPC477924
0.8434	Intermediate Similarity	NPC470711
0.8434	Intermediate Similarity	NPC34019
0.8434	Intermediate Similarity	NPC470758
0.8427	Intermediate Similarity	NPC471952
0.8421	Intermediate Similarity	NPC476897
0.8415	Intermediate Similarity	NPC230704
0.8415	Intermediate Similarity	NPC70982
0.8415	Intermediate Similarity	NPC185536
0.8409	Intermediate Similarity	NPC24277
0.8409	Intermediate Similarity	NPC293287
0.8409	Intermediate Similarity	NPC152808
0.8409	Intermediate Similarity	NPC125399
0.8409	Intermediate Similarity	NPC201273
0.8409	Intermediate Similarity	NPC299068
0.8391	Intermediate Similarity	NPC475798
0.8391	Intermediate Similarity	NPC127606
0.8391	Intermediate Similarity	NPC255882
0.8391	Intermediate Similarity	NPC124172
0.8391	Intermediate Similarity	NPC238992
0.8391	Intermediate Similarity	NPC474047
0.8387	Intermediate Similarity	NPC114743
0.8387	Intermediate Similarity	NPC72204
0.8387	Intermediate Similarity	NPC195366
0.8372	Intermediate Similarity	NPC470049
0.8372	Intermediate Similarity	NPC189972
0.8372	Intermediate Similarity	NPC87489
0.8372	Intermediate Similarity	NPC50964
0.8372	Intermediate Similarity	NPC202389
0.837	Intermediate Similarity	NPC65402
0.837	Intermediate Similarity	NPC477605
0.837	Intermediate Similarity	NPC127718
0.8353	Intermediate Similarity	NPC241290
0.8353	Intermediate Similarity	NPC164840
0.8353	Intermediate Similarity	NPC209944
0.8352	Intermediate Similarity	NPC110923
0.8352	Intermediate Similarity	NPC74296
0.8333	Intermediate Similarity	NPC83351
0.8333	Intermediate Similarity	NPC11908
0.8333	Intermediate Similarity	NPC259875
0.8333	Intermediate Similarity	NPC187785
0.8333	Intermediate Similarity	NPC275910
0.8333	Intermediate Similarity	NPC167891
0.8333	Intermediate Similarity	NPC109744
0.8333	Intermediate Similarity	NPC473943
0.8313	Intermediate Similarity	NPC189883
0.8313	Intermediate Similarity	NPC91573
0.8313	Intermediate Similarity	NPC240604
0.8313	Intermediate Similarity	NPC244488
0.8313	Intermediate Similarity	NPC321016
0.8313	Intermediate Similarity	NPC107059
0.8313	Intermediate Similarity	NPC477925
0.8313	Intermediate Similarity	NPC300324
0.8313	Intermediate Similarity	NPC470749
0.8313	Intermediate Similarity	NPC247325
0.8313	Intermediate Similarity	NPC274079
0.8313	Intermediate Similarity	NPC321381
0.8298	Intermediate Similarity	NPC261807
0.8298	Intermediate Similarity	NPC477226
0.8295	Intermediate Similarity	NPC318390
0.8295	Intermediate Similarity	NPC470360
0.8295	Intermediate Similarity	NPC274448
0.8293	Intermediate Similarity	NPC254509
0.8293	Intermediate Similarity	NPC145552
0.8293	Intermediate Similarity	NPC196358
0.8293	Intermediate Similarity	NPC49168
0.8293	Intermediate Similarity	NPC5046
0.828	Intermediate Similarity	NPC8774
0.8276	Intermediate Similarity	NPC477818
0.8276	Intermediate Similarity	NPC253402
0.8276	Intermediate Similarity	NPC470384
0.8276	Intermediate Similarity	NPC470558
0.8276	Intermediate Similarity	NPC216420
0.8276	Intermediate Similarity	NPC141941
0.8276	Intermediate Similarity	NPC85095
0.8276	Intermediate Similarity	NPC193870
0.8276	Intermediate Similarity	NPC211135
0.8276	Intermediate Similarity	NPC159168
0.8256	Intermediate Similarity	NPC474683
0.8256	Intermediate Similarity	NPC7505
0.8256	Intermediate Similarity	NPC476646
0.8256	Intermediate Similarity	NPC474731
0.8256	Intermediate Similarity	NPC47761
0.8256	Intermediate Similarity	NPC82986
0.8256	Intermediate Similarity	NPC474752
0.8256	Intermediate Similarity	NPC474759
0.8256	Intermediate Similarity	NPC470383
0.8242	Intermediate Similarity	NPC295668
0.8235	Intermediate Similarity	NPC472463
0.8235	Intermediate Similarity	NPC1319
0.8235	Intermediate Similarity	NPC5604
0.8222	Intermediate Similarity	NPC280556
0.8214	Intermediate Similarity	NPC260301
0.8214	Intermediate Similarity	NPC91594
0.8214	Intermediate Similarity	NPC318495
0.8214	Intermediate Similarity	NPC212241
0.8214	Intermediate Similarity	NPC138502
0.8214	Intermediate Similarity	NPC248830
0.8214	Intermediate Similarity	NPC198968
0.8214	Intermediate Similarity	NPC214570
0.8214	Intermediate Similarity	NPC119355
0.8214	Intermediate Similarity	NPC307336
0.8214	Intermediate Similarity	NPC155986
0.8202	Intermediate Similarity	NPC121981
0.8202	Intermediate Similarity	NPC6605
0.8202	Intermediate Similarity	NPC477604
0.8202	Intermediate Similarity	NPC237344
0.8193	Intermediate Similarity	NPC22105
0.8193	Intermediate Similarity	NPC230301
0.8193	Intermediate Similarity	NPC200243
0.8193	Intermediate Similarity	NPC471723

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 NPC67872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1665
0.2-0.3	4243
0.3-0.4	2157
0.4-0.5	484
0.5-0.6	212
0.6-0.7	173
0.7-0.8	43
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8795	High Similarity	NPD7525	Registered
0.8193	Intermediate Similarity	NPD6942	Approved
0.8193	Intermediate Similarity	NPD7339	Approved
0.7882	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6933	Approved
0.7841	Intermediate Similarity	NPD6902	Approved
0.7816	Intermediate Similarity	NPD7645	Phase 2
0.7816	Intermediate Similarity	NPD6929	Approved
0.7778	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6931	Approved
0.7727	Intermediate Similarity	NPD6930	Phase 2
0.7717	Intermediate Similarity	NPD7524	Approved
0.7717	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD6695	Phase 3
0.7647	Intermediate Similarity	NPD6926	Approved
0.7647	Intermediate Similarity	NPD6924	Approved
0.759	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD6925	Approved
0.7586	Intermediate Similarity	NPD5776	Phase 2
0.7582	Intermediate Similarity	NPD4786	Approved
0.7528	Intermediate Similarity	NPD7514	Phase 3
0.75	Intermediate Similarity	NPD7145	Approved
0.7412	Intermediate Similarity	NPD7150	Approved
0.7412	Intermediate Similarity	NPD7152	Approved
0.7412	Intermediate Similarity	NPD7151	Approved
0.74	Intermediate Similarity	NPD7640	Approved
0.74	Intermediate Similarity	NPD7639	Approved
0.7381	Intermediate Similarity	NPD6923	Approved
0.7381	Intermediate Similarity	NPD6922	Approved
0.7368	Intermediate Similarity	NPD5328	Approved
0.7363	Intermediate Similarity	NPD3667	Approved
0.734	Intermediate Similarity	NPD7750	Discontinued
0.7333	Intermediate Similarity	NPD7509	Discontinued
0.7333	Intermediate Similarity	NPD7332	Phase 2
0.7312	Intermediate Similarity	NPD6893	Approved
0.7303	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD7638	Approved
0.7294	Intermediate Similarity	NPD7143	Approved
0.7294	Intermediate Similarity	NPD7144	Approved
0.7255	Intermediate Similarity	NPD5211	Phase 2
0.7241	Intermediate Similarity	NPD4784	Approved
0.7241	Intermediate Similarity	NPD4785	Approved
0.7234	Intermediate Similarity	NPD3618	Phase 1
0.7216	Intermediate Similarity	NPD6079	Approved
0.7209	Intermediate Similarity	NPD4243	Approved
0.72	Intermediate Similarity	NPD4755	Approved
0.7191	Intermediate Similarity	NPD6932	Approved
0.7182	Intermediate Similarity	NPD7115	Discovery
0.7159	Intermediate Similarity	NPD8264	Approved
0.7143	Intermediate Similarity	NPD4748	Discontinued
0.7143	Intermediate Similarity	NPD4202	Approved
0.7143	Intermediate Similarity	NPD6399	Phase 3
0.7129	Intermediate Similarity	NPD4225	Approved
0.7128	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5141	Approved
0.7065	Intermediate Similarity	NPD6898	Phase 1
0.7059	Intermediate Similarity	NPD4696	Approved
0.7059	Intermediate Similarity	NPD4700	Approved
0.7059	Intermediate Similarity	NPD5286	Approved
0.7059	Intermediate Similarity	NPD5285	Approved
0.7041	Intermediate Similarity	NPD7087	Discontinued
0.7033	Intermediate Similarity	NPD6683	Phase 2
0.699	Remote Similarity	NPD4159	Approved
0.6964	Remote Similarity	NPD7327	Approved
0.6964	Remote Similarity	NPD7328	Approved
0.6931	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5222	Approved
0.6931	Remote Similarity	NPD4697	Phase 3
0.6931	Remote Similarity	NPD5221	Approved
0.693	Remote Similarity	NPD8033	Approved
0.6923	Remote Similarity	NPD5224	Approved
0.6923	Remote Similarity	NPD5226	Approved
0.6923	Remote Similarity	NPD5225	Approved
0.6923	Remote Similarity	NPD4633	Approved
0.6903	Remote Similarity	NPD7516	Approved
0.6887	Remote Similarity	NPD5739	Approved
0.6887	Remote Similarity	NPD7128	Approved
0.6887	Remote Similarity	NPD6402	Approved
0.6887	Remote Similarity	NPD6675	Approved
0.6869	Remote Similarity	NPD7515	Phase 2
0.6869	Remote Similarity	NPD8034	Phase 2
0.6869	Remote Similarity	NPD7637	Suspended
0.6869	Remote Similarity	NPD8035	Phase 2
0.6863	Remote Similarity	NPD5173	Approved
0.6857	Remote Similarity	NPD5175	Approved
0.6857	Remote Similarity	NPD5174	Approved
0.6842	Remote Similarity	NPD3133	Approved
0.6842	Remote Similarity	NPD3668	Phase 3
0.6842	Remote Similarity	NPD3666	Approved
0.6842	Remote Similarity	NPD8294	Approved
0.6842	Remote Similarity	NPD8377	Approved
0.6842	Remote Similarity	NPD3665	Phase 1
0.6837	Remote Similarity	NPD4753	Phase 2
0.6827	Remote Similarity	NPD5223	Approved
0.6789	Remote Similarity	NPD4634	Approved
0.6783	Remote Similarity	NPD8380	Approved
0.6783	Remote Similarity	NPD8379	Approved
0.6783	Remote Similarity	NPD8296	Approved
0.6783	Remote Similarity	NPD8378	Approved
0.6783	Remote Similarity	NPD8335	Approved
0.6778	Remote Similarity	NPD4190	Phase 3
0.6778	Remote Similarity	NPD5275	Approved
0.6762	Remote Similarity	NPD7632	Discontinued
0.6759	Remote Similarity	NPD6899	Approved
0.6759	Remote Similarity	NPD6881	Approved
0.6759	Remote Similarity	NPD7320	Approved
0.6729	Remote Similarity	NPD4767	Approved
0.6729	Remote Similarity	NPD4768	Approved
0.6698	Remote Similarity	NPD4754	Approved
0.6697	Remote Similarity	NPD6373	Approved
0.6697	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6636	Remote Similarity	NPD6883	Approved
0.6636	Remote Similarity	NPD7290	Approved
0.6636	Remote Similarity	NPD7102	Approved
0.663	Remote Similarity	NPD6116	Phase 1
0.6606	Remote Similarity	NPD4730	Approved
0.6606	Remote Similarity	NPD5128	Approved
0.6606	Remote Similarity	NPD4729	Approved
0.66	Remote Similarity	NPD7136	Phase 2
0.6577	Remote Similarity	NPD6869	Approved
0.6577	Remote Similarity	NPD6847	Approved
0.6577	Remote Similarity	NPD6649	Approved
0.6577	Remote Similarity	NPD8130	Phase 1
0.6577	Remote Similarity	NPD6650	Approved
0.6577	Remote Similarity	NPD6617	Approved
0.6569	Remote Similarity	NPD7748	Approved
0.6562	Remote Similarity	NPD4788	Approved
0.6555	Remote Similarity	NPD7507	Approved
0.6548	Remote Similarity	NPD368	Approved
0.6545	Remote Similarity	NPD6012	Approved
0.6545	Remote Similarity	NPD6013	Approved
0.6545	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD6084	Phase 2
0.6538	Remote Similarity	NPD6083	Phase 2
0.6538	Remote Similarity	NPD7902	Approved
0.6531	Remote Similarity	NPD5279	Phase 3
0.6522	Remote Similarity	NPD6117	Approved
0.6518	Remote Similarity	NPD6882	Approved
0.6517	Remote Similarity	NPD4787	Phase 1
0.6514	Remote Similarity	NPD6412	Phase 2
0.6509	Remote Similarity	NPD5344	Discontinued
0.6505	Remote Similarity	NPD4629	Approved
0.6505	Remote Similarity	NPD5210	Approved
0.6496	Remote Similarity	NPD7503	Approved
0.6486	Remote Similarity	NPD5250	Approved
0.6486	Remote Similarity	NPD5251	Approved
0.6486	Remote Similarity	NPD5249	Phase 3
0.6486	Remote Similarity	NPD5248	Approved
0.6486	Remote Similarity	NPD5247	Approved
0.6476	Remote Similarity	NPD5290	Discontinued
0.646	Remote Similarity	NPD4632	Approved
0.6458	Remote Similarity	NPD4221	Approved
0.6458	Remote Similarity	NPD4223	Phase 3
0.6455	Remote Similarity	NPD6011	Approved
0.6444	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5329	Approved
0.6429	Remote Similarity	NPD5215	Approved
0.6429	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5217	Approved
0.6429	Remote Similarity	NPD5216	Approved
0.6422	Remote Similarity	NPD6640	Phase 3
0.6421	Remote Similarity	NPD4819	Approved
0.6421	Remote Similarity	NPD4821	Approved
0.6421	Remote Similarity	NPD4822	Approved
0.6421	Remote Similarity	NPD4820	Approved
0.6396	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7319	Approved
0.6383	Remote Similarity	NPD6115	Approved
0.6383	Remote Similarity	NPD4268	Approved
0.6383	Remote Similarity	NPD6118	Approved
0.6383	Remote Similarity	NPD4271	Approved
0.6383	Remote Similarity	NPD6114	Approved
0.6383	Remote Similarity	NPD6697	Approved
0.6383	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5169	Approved
0.6339	Remote Similarity	NPD5135	Approved
0.6339	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4197	Approved
0.6306	Remote Similarity	NPD5168	Approved
0.6306	Remote Similarity	NPD6686	Approved
0.6304	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5127	Approved
0.6273	Remote Similarity	NPD6008	Approved
0.6271	Remote Similarity	NPD6059	Approved
0.6271	Remote Similarity	NPD6319	Approved
0.6271	Remote Similarity	NPD6054	Approved
0.6263	Remote Similarity	NPD1696	Phase 3
0.626	Remote Similarity	NPD3094	Phase 2
0.625	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7900	Approved
0.625	Remote Similarity	NPD7604	Phase 2

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