NPASS Compound

Structure

NPC226986 OpenBabel07101718302D 30 33 0 0 1 0 0 0 0 0999 V2000 1.4576 -2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1084 -3.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3709 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 -1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8709 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5630 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9195 0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 0.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0646 -1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1133 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 -3.3002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5775 -0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2650 -1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.8002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2472 -0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0896 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.0801 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 -2.9793 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -3.8002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8885 -1.7907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6634 -1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1133 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2424 -2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 2 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 22 1 0 0 0 0 9 16 1 0 0 0 0 9 18 2 0 0 0 0 11 17 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 12 21 1 0 0 0 0 13 25 2 0 0 0 0 13 29 1 0 0 0 0 14 26 2 0 0 0 0 14 30 1 0 0 0 0 15 10 1 1 0 0 0 15 16 1 0 0 0 0 16 27 2 0 0 0 0 17 20 1 0 0 0 0 17 29 1 1 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 19 23 1 1 0 0 0 19 30 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 1 0 0 0 21 24 1 0 0 0 0 21 28 2 0 0 0 0 23 6 1 1 0 0 0 24 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.2
Volume:	426.357
LogP:	2.679
LogD:	2.071
LogS:	-4.399
# Rotatable Bonds:	4
TPSA:	86.74
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.644
Synthetic Accessibility Score:	6.059
Fsp3:	0.667
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:	-4.917
MDCK Permeability:	2.237106309621595e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.014
20% Bioavailability (F20%):	0.988
30% Bioavailability (F30%):	0.829

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.584
Plasma Protein Binding (PPB):	84.66352081298828%
Volume Distribution (VD):	1.41
Pgp-substrate:	19.427833557128906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.081
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.865
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.054
CYP3A4-inhibitor:	0.394
CYP3A4-substrate:	0.902

ADMET: Excretion

Clearance (CL):	3.019
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.067
Drug-inuced Liver Injury (DILI):	0.384
AMES Toxicity:	0.775
Rat Oral Acute Toxicity:	0.578
Maximum Recommended Daily Dose:	0.783
Skin Sensitization:	0.107
Carcinogencity:	0.854
Eye Corrosion:	0.021
Eye Irritation:	0.017
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC226986

Natural Product ID:	NPC226986
*Common Name:**	ZQLDTRWXXBIPHC-GLFHXRGXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	ZQLDTRWXXBIPHC-GLFHXRGXSA-N
Standard InCHI:	InChI=1S/C24H30O6/c1-12-15-10-24(21(12)28)11-17(29-13(2)25)20-22(4,5)8-7-19(30-14(3)26)23(20,6)18(24)9-16(15)27/h9,15,17,19-20H,1,7-8,10-11H2,2-6H3/t15-,17+,19+,20-,23-,24+/m1/s1
SMILES:	C=C1[C@H]2C[C@@]3(C[C@@H]([C@@H]4C(C)(C)CC[C@@H]([C@@]4(C)C3=CC2=O)OC(=O)C)OC(=O)C)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496474
PubChem CID:	25019496
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO33117	jungermannia atrobrunnea	Species	Jungermanniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18665642]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	128.0	ug.mL-1	PMID[496092]

☑ 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 NPC226986 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	230
0.1-0.2	1373
0.2-0.3	5273
0.3-0.4	10549
0.4-0.5	10829
0.5-0.6	6511
0.6-0.7	5430
0.7-0.8	2330
0.8-0.85	159
0.85-0.9	10
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC23680
0.8866	High Similarity	NPC81530
0.8854	High Similarity	NPC176845
0.8776	High Similarity	NPC136289
0.875	High Similarity	NPC292133
0.8737	High Similarity	NPC274417
0.8723	High Similarity	NPC79117
0.8632	High Similarity	NPC269729
0.86	High Similarity	NPC189616
0.8557	High Similarity	NPC84335
0.8557	High Similarity	NPC38530
0.8557	High Similarity	NPC216904
0.8511	High Similarity	NPC152467
0.85	High Similarity	NPC36321
0.8478	Intermediate Similarity	NPC471042
0.8469	Intermediate Similarity	NPC112753
0.8469	Intermediate Similarity	NPC114274
0.8469	Intermediate Similarity	NPC275439
0.8421	Intermediate Similarity	NPC218301
0.8384	Intermediate Similarity	NPC475202
0.8384	Intermediate Similarity	NPC475392
0.8384	Intermediate Similarity	NPC476274
0.8384	Intermediate Similarity	NPC475385
0.8384	Intermediate Similarity	NPC88198
0.8351	Intermediate Similarity	NPC255809
0.8351	Intermediate Similarity	NPC317586
0.8351	Intermediate Similarity	NPC470016
0.835	Intermediate Similarity	NPC295244
0.8333	Intermediate Similarity	NPC474185
0.8333	Intermediate Similarity	NPC102352
0.8317	Intermediate Similarity	NPC254202
0.8317	Intermediate Similarity	NPC33973
0.8317	Intermediate Similarity	NPC70967
0.8317	Intermediate Similarity	NPC275583
0.8317	Intermediate Similarity	NPC159442
0.8316	Intermediate Similarity	NPC474842
0.8316	Intermediate Similarity	NPC475965
0.8316	Intermediate Similarity	NPC328141
0.83	Intermediate Similarity	NPC476240
0.83	Intermediate Similarity	NPC224720
0.83	Intermediate Similarity	NPC124211
0.83	Intermediate Similarity	NPC476223
0.8283	Intermediate Similarity	NPC252295
0.8265	Intermediate Similarity	NPC104568
0.8265	Intermediate Similarity	NPC111684
0.8265	Intermediate Similarity	NPC58052
0.8252	Intermediate Similarity	NPC220974
0.8252	Intermediate Similarity	NPC133422
0.8252	Intermediate Similarity	NPC44063
0.8247	Intermediate Similarity	NPC159410
0.8247	Intermediate Similarity	NPC470697
0.8247	Intermediate Similarity	NPC56525
0.8247	Intermediate Similarity	NPC166906
0.8235	Intermediate Similarity	NPC135854
0.8235	Intermediate Similarity	NPC470251
0.8235	Intermediate Similarity	NPC96268
0.8235	Intermediate Similarity	NPC216245
0.8235	Intermediate Similarity	NPC2436
0.8229	Intermediate Similarity	NPC297265
0.8218	Intermediate Similarity	NPC271266
0.8218	Intermediate Similarity	NPC308351
0.8218	Intermediate Similarity	NPC53222
0.8211	Intermediate Similarity	NPC73995
0.8211	Intermediate Similarity	NPC469546
0.8211	Intermediate Similarity	NPC474679
0.8208	Intermediate Similarity	NPC71348
0.82	Intermediate Similarity	NPC157787
0.82	Intermediate Similarity	NPC51370
0.82	Intermediate Similarity	NPC287833
0.8191	Intermediate Similarity	NPC30421
0.819	Intermediate Similarity	NPC197428
0.8182	Intermediate Similarity	NPC170131
0.8182	Intermediate Similarity	NPC43747
0.8182	Intermediate Similarity	NPC108078
0.8182	Intermediate Similarity	NPC10864
0.8173	Intermediate Similarity	NPC277017
0.8173	Intermediate Similarity	NPC469844
0.8173	Intermediate Similarity	NPC154608
0.8173	Intermediate Similarity	NPC192813
0.8172	Intermediate Similarity	NPC323765
0.8163	Intermediate Similarity	NPC469599
0.8163	Intermediate Similarity	NPC98639
0.8155	Intermediate Similarity	NPC470267
0.8144	Intermediate Similarity	NPC294263
0.8144	Intermediate Similarity	NPC107674
0.8144	Intermediate Similarity	NPC141497
0.8144	Intermediate Similarity	NPC170220
0.8137	Intermediate Similarity	NPC236390
0.8137	Intermediate Similarity	NPC264048
0.8137	Intermediate Similarity	NPC95585
0.8137	Intermediate Similarity	NPC282233
0.8137	Intermediate Similarity	NPC216114
0.8132	Intermediate Similarity	NPC475665
0.8131	Intermediate Similarity	NPC472929
0.8125	Intermediate Similarity	NPC471896
0.8119	Intermediate Similarity	NPC473514
0.8119	Intermediate Similarity	NPC310981
0.8113	Intermediate Similarity	NPC470960
0.8105	Intermediate Similarity	NPC215831
0.8105	Intermediate Similarity	NPC328539
0.81	Intermediate Similarity	NPC478056
0.81	Intermediate Similarity	NPC89099
0.8095	Intermediate Similarity	NPC2766
0.8085	Intermediate Similarity	NPC264127
0.8085	Intermediate Similarity	NPC195640
0.8081	Intermediate Similarity	NPC96859
0.8081	Intermediate Similarity	NPC95565
0.8081	Intermediate Similarity	NPC29410
0.8081	Intermediate Similarity	NPC125622
0.8081	Intermediate Similarity	NPC328162
0.8081	Intermediate Similarity	NPC192428
0.8081	Intermediate Similarity	NPC471775
0.8081	Intermediate Similarity	NPC200054
0.8081	Intermediate Similarity	NPC307164
0.8081	Intermediate Similarity	NPC13949
0.8081	Intermediate Similarity	NPC305483
0.8077	Intermediate Similarity	NPC3316
0.8077	Intermediate Similarity	NPC144854
0.8065	Intermediate Similarity	NPC320801
0.8061	Intermediate Similarity	NPC477130
0.8061	Intermediate Similarity	NPC84893
0.8061	Intermediate Similarity	NPC477129
0.8061	Intermediate Similarity	NPC471040
0.8058	Intermediate Similarity	NPC98603
0.8058	Intermediate Similarity	NPC235889
0.8058	Intermediate Similarity	NPC84928
0.8043	Intermediate Similarity	NPC470813
0.8041	Intermediate Similarity	NPC470230
0.8041	Intermediate Similarity	NPC212301
0.8041	Intermediate Similarity	NPC26888
0.8041	Intermediate Similarity	NPC168027
0.8041	Intermediate Similarity	NPC185936
0.8041	Intermediate Similarity	NPC110657
0.8041	Intermediate Similarity	NPC250753
0.8041	Intermediate Similarity	NPC86266
0.8039	Intermediate Similarity	NPC22388
0.8039	Intermediate Similarity	NPC195290
0.8039	Intermediate Similarity	NPC204450
0.8039	Intermediate Similarity	NPC163249
0.8039	Intermediate Similarity	NPC293753
0.8039	Intermediate Similarity	NPC234892
0.8037	Intermediate Similarity	NPC205534
0.8037	Intermediate Similarity	NPC264634
0.8021	Intermediate Similarity	NPC119416
0.8021	Intermediate Similarity	NPC473039
0.8021	Intermediate Similarity	NPC11611
0.802	Intermediate Similarity	NPC316964
0.802	Intermediate Similarity	NPC293866
0.802	Intermediate Similarity	NPC470906
0.802	Intermediate Similarity	NPC104861
0.8019	Intermediate Similarity	NPC239097
0.8019	Intermediate Similarity	NPC286880
0.8019	Intermediate Similarity	NPC253906
0.8	Intermediate Similarity	NPC106557
0.8	Intermediate Similarity	NPC189075
0.8	Intermediate Similarity	NPC470269
0.8	Intermediate Similarity	NPC275539
0.8	Intermediate Similarity	NPC19412
0.8	Intermediate Similarity	NPC474343
0.8	Intermediate Similarity	NPC121339
0.8	Intermediate Similarity	NPC473456
0.7982	Intermediate Similarity	NPC270958
0.7981	Intermediate Similarity	NPC475571
0.7981	Intermediate Similarity	NPC181265
0.7981	Intermediate Similarity	NPC278628
0.7981	Intermediate Similarity	NPC231530
0.7981	Intermediate Similarity	NPC181357
0.798	Intermediate Similarity	NPC241156
0.798	Intermediate Similarity	NPC183012
0.798	Intermediate Similarity	NPC139570
0.798	Intermediate Similarity	NPC139459
0.7979	Intermediate Similarity	NPC470223
0.7979	Intermediate Similarity	NPC110405
0.7963	Intermediate Similarity	NPC202889
0.7963	Intermediate Similarity	NPC52634
0.7961	Intermediate Similarity	NPC140723
0.7959	Intermediate Similarity	NPC470375
0.7959	Intermediate Similarity	NPC476416
0.7959	Intermediate Similarity	NPC470376
0.7959	Intermediate Similarity	NPC470224
0.7959	Intermediate Similarity	NPC109414
0.7957	Intermediate Similarity	NPC271784
0.7957	Intermediate Similarity	NPC469561
0.7944	Intermediate Similarity	NPC472928
0.7941	Intermediate Similarity	NPC115862
0.7938	Intermediate Similarity	NPC111585
0.7938	Intermediate Similarity	NPC148414
0.7938	Intermediate Similarity	NPC175628
0.7925	Intermediate Similarity	NPC153239
0.7925	Intermediate Similarity	NPC258543
0.7925	Intermediate Similarity	NPC112457
0.7925	Intermediate Similarity	NPC41405
0.7925	Intermediate Similarity	NPC241927
0.7921	Intermediate Similarity	NPC162459
0.7921	Intermediate Similarity	NPC471038
0.7921	Intermediate Similarity	NPC194196
0.7921	Intermediate Similarity	NPC98837
0.7921	Intermediate Similarity	NPC28864
0.7921	Intermediate Similarity	NPC20479
0.7921	Intermediate Similarity	NPC38471

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 NPC226986 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	1610
0.2-0.3	3999
0.3-0.4	2187
0.4-0.5	708
0.5-0.6	184
0.6-0.7	116
0.7-0.8	114
0.8-0.85	39
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8526	High Similarity	NPD6399	Phase 3
0.8515	High Similarity	NPD6008	Approved
0.8438	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7900	Approved
0.8286	Intermediate Similarity	NPD6650	Approved
0.8286	Intermediate Similarity	NPD6649	Approved
0.8269	Intermediate Similarity	NPD6372	Approved
0.8269	Intermediate Similarity	NPD6373	Approved
0.8252	Intermediate Similarity	NPD5697	Approved
0.8191	Intermediate Similarity	NPD3573	Approved
0.8182	Intermediate Similarity	NPD7902	Approved
0.8173	Intermediate Similarity	NPD6899	Approved
0.8173	Intermediate Similarity	NPD6881	Approved
0.8173	Intermediate Similarity	NPD6011	Approved
0.8155	Intermediate Similarity	NPD6675	Approved
0.8155	Intermediate Similarity	NPD7128	Approved
0.8155	Intermediate Similarity	NPD6402	Approved
0.8155	Intermediate Similarity	NPD5739	Approved
0.8105	Intermediate Similarity	NPD6672	Approved
0.8105	Intermediate Similarity	NPD5737	Approved
0.8095	Intermediate Similarity	NPD6012	Approved
0.8095	Intermediate Similarity	NPD6014	Approved
0.8095	Intermediate Similarity	NPD6013	Approved
0.8085	Intermediate Similarity	NPD7146	Approved
0.8085	Intermediate Similarity	NPD7521	Approved
0.8085	Intermediate Similarity	NPD7334	Approved
0.8085	Intermediate Similarity	NPD5330	Approved
0.8085	Intermediate Similarity	NPD6684	Approved
0.8085	Intermediate Similarity	NPD6409	Approved
0.8081	Intermediate Similarity	NPD4697	Phase 3
0.8077	Intermediate Similarity	NPD5701	Approved
0.8041	Intermediate Similarity	NPD6079	Approved
0.8021	Intermediate Similarity	NPD5328	Approved
0.8019	Intermediate Similarity	NPD7290	Approved
0.8019	Intermediate Similarity	NPD6883	Approved
0.8019	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD7320	Approved
0.798	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7944	Intermediate Similarity	NPD6869	Approved
0.7944	Intermediate Similarity	NPD6847	Approved
0.7944	Intermediate Similarity	NPD8130	Phase 1
0.7944	Intermediate Similarity	NPD6617	Approved
0.7921	Intermediate Similarity	NPD5696	Approved
0.7917	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD6903	Approved
0.79	Intermediate Similarity	NPD5222	Approved
0.79	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD5221	Approved
0.7895	Intermediate Similarity	NPD3618	Phase 1
0.7879	Intermediate Similarity	NPD7748	Approved
0.787	Intermediate Similarity	NPD6882	Approved
0.787	Intermediate Similarity	NPD8297	Approved
0.7843	Intermediate Similarity	NPD5285	Approved
0.7843	Intermediate Similarity	NPD5286	Approved
0.7843	Intermediate Similarity	NPD4696	Approved
0.7822	Intermediate Similarity	NPD5173	Approved
0.7822	Intermediate Similarity	NPD4755	Approved
0.7778	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD5223	Approved
0.77	Intermediate Similarity	NPD6001	Approved
0.7692	Intermediate Similarity	NPD5224	Approved
0.7692	Intermediate Similarity	NPD4633	Approved
0.7692	Intermediate Similarity	NPD5225	Approved
0.7692	Intermediate Similarity	NPD5211	Phase 2
0.7692	Intermediate Similarity	NPD5226	Approved
0.7677	Intermediate Similarity	NPD8035	Phase 2
0.7677	Intermediate Similarity	NPD8034	Phase 2
0.7677	Intermediate Similarity	NPD7515	Phase 2
0.767	Intermediate Similarity	NPD4700	Approved
0.7658	Intermediate Similarity	NPD6274	Approved
0.7653	Intermediate Similarity	NPD6904	Approved
0.7653	Intermediate Similarity	NPD6673	Approved
0.7653	Intermediate Similarity	NPD6080	Approved
0.7636	Intermediate Similarity	NPD4632	Approved
0.7619	Intermediate Similarity	NPD5175	Approved
0.7619	Intermediate Similarity	NPD5174	Approved
0.7604	Intermediate Similarity	NPD1694	Approved
0.76	Intermediate Similarity	NPD4202	Approved
0.7589	Intermediate Similarity	NPD6317	Approved
0.7551	Intermediate Similarity	NPD5208	Approved
0.7547	Intermediate Similarity	NPD5141	Approved
0.7522	Intermediate Similarity	NPD6313	Approved
0.7522	Intermediate Similarity	NPD6314	Approved
0.7522	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD3668	Phase 3
0.75	Intermediate Similarity	NPD6868	Approved
0.75	Intermediate Similarity	NPD5693	Phase 1
0.75	Intermediate Similarity	NPD4786	Approved
0.7478	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7476	Intermediate Similarity	NPD6084	Phase 2
0.7476	Intermediate Similarity	NPD6083	Phase 2
0.7474	Intermediate Similarity	NPD3667	Approved
0.7474	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7101	Approved
0.7456	Intermediate Similarity	NPD7100	Approved
0.7453	Intermediate Similarity	NPD4754	Approved
0.7451	Intermediate Similarity	NPD4629	Approved
0.7451	Intermediate Similarity	NPD5210	Approved
0.7451	Intermediate Similarity	NPD5695	Phase 3
0.7434	Intermediate Similarity	NPD7115	Discovery
0.7434	Intermediate Similarity	NPD6009	Approved
0.74	Intermediate Similarity	NPD5692	Phase 3
0.74	Intermediate Similarity	NPD5207	Approved
0.7391	Intermediate Similarity	NPD6319	Approved
0.7347	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6098	Approved
0.7339	Intermediate Similarity	NPD4729	Approved
0.7339	Intermediate Similarity	NPD5128	Approved
0.7339	Intermediate Similarity	NPD4730	Approved
0.7328	Intermediate Similarity	NPD5983	Phase 2
0.7327	Intermediate Similarity	NPD6050	Approved
0.7327	Intermediate Similarity	NPD5694	Approved
0.7327	Intermediate Similarity	NPD5281	Approved
0.7327	Intermediate Similarity	NPD5284	Approved
0.732	Intermediate Similarity	NPD3665	Phase 1
0.732	Intermediate Similarity	NPD3133	Approved
0.732	Intermediate Similarity	NPD3666	Approved
0.7315	Intermediate Similarity	NPD4768	Approved
0.7315	Intermediate Similarity	NPD4767	Approved
0.7248	Intermediate Similarity	NPD6614	Approved
0.7238	Intermediate Similarity	NPD7638	Approved
0.7212	Intermediate Similarity	NPD7732	Phase 3
0.7207	Intermediate Similarity	NPD5251	Approved
0.7207	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5249	Phase 3
0.7207	Intermediate Similarity	NPD5135	Approved
0.7207	Intermediate Similarity	NPD5169	Approved
0.7207	Intermediate Similarity	NPD4634	Approved
0.7207	Intermediate Similarity	NPD5247	Approved
0.7207	Intermediate Similarity	NPD5250	Approved
0.7207	Intermediate Similarity	NPD5248	Approved
0.7203	Intermediate Similarity	NPD7604	Phase 2
0.7182	Intermediate Similarity	NPD5168	Approved
0.7179	Intermediate Similarity	NPD6908	Approved
0.7179	Intermediate Similarity	NPD6909	Approved
0.717	Intermediate Similarity	NPD7640	Approved
0.717	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD5215	Approved
0.7143	Intermediate Similarity	NPD5127	Approved
0.7143	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD5216	Approved
0.7143	Intermediate Similarity	NPD5217	Approved
0.7129	Intermediate Similarity	NPD4753	Phase 2
0.7113	Intermediate Similarity	NPD4221	Approved
0.7113	Intermediate Similarity	NPD4223	Phase 3
0.7094	Intermediate Similarity	NPD6054	Approved
0.7091	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6616	Approved
0.7083	Intermediate Similarity	NPD4695	Discontinued
0.7083	Intermediate Similarity	NPD6336	Discontinued
0.7075	Intermediate Similarity	NPD4225	Approved
0.7071	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6016	Approved
0.7034	Intermediate Similarity	NPD6015	Approved
0.7033	Intermediate Similarity	NPD4691	Approved
0.7033	Intermediate Similarity	NPD4747	Approved
0.7025	Intermediate Similarity	NPD7078	Approved
0.7	Intermediate Similarity	NPD5279	Phase 3
0.699	Remote Similarity	NPD6411	Approved
0.6975	Remote Similarity	NPD5988	Approved
0.6975	Remote Similarity	NPD6370	Approved
0.6972	Remote Similarity	NPD6052	Approved
0.697	Remote Similarity	NPD4197	Approved
0.6967	Remote Similarity	NPD7736	Approved
0.6957	Remote Similarity	NPD5167	Approved
0.6952	Remote Similarity	NPD5654	Approved
0.6949	Remote Similarity	NPD6059	Approved
0.6923	Remote Similarity	NPD4137	Phase 3
0.6903	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5329	Approved
0.6887	Remote Similarity	NPD7614	Phase 1
0.6885	Remote Similarity	NPD8293	Discontinued
0.6832	Remote Similarity	NPD4693	Phase 3
0.6832	Remote Similarity	NPD4689	Approved
0.6832	Remote Similarity	NPD4138	Approved
0.6832	Remote Similarity	NPD4688	Approved
0.6832	Remote Similarity	NPD5205	Approved
0.6832	Remote Similarity	NPD5690	Phase 2
0.6832	Remote Similarity	NPD4690	Approved
0.6822	Remote Similarity	NPD5959	Approved
0.6809	Remote Similarity	NPD4058	Approved
0.6796	Remote Similarity	NPD6051	Approved
0.6796	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6101	Approved
0.6792	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6412	Phase 2
0.6777	Remote Similarity	NPD8328	Phase 3
0.6735	Remote Similarity	NPD7525	Registered
0.6727	Remote Similarity	NPD5091	Approved
0.6701	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7507	Approved
0.6638	Remote Similarity	NPD6053	Discontinued
0.6633	Remote Similarity	NPD4195	Approved
0.6632	Remote Similarity	NPD4687	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