NPASS Compound

Structure

CID285513 OpenBabel06191716092D 44 45 0 0 1 0 0 0 0 0999 V2000 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2942 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 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 9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 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 8.6603 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 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6603 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7942 -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 7.7942 1.5000 0.0000 C 0 0 0 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 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -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 2 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1340 3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 34 1 0 0 0 0 8 34 1 0 0 0 0 9 35 1 0 0 0 0 10 35 1 0 0 0 0 12 15 1 0 0 0 0 12 22 2 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 14 23 2 0 0 0 0 16 31 1 0 0 0 0 17 32 1 0 0 0 0 18 19 1 0 0 0 0 18 33 1 0 0 0 0 19 36 1 0 0 0 0 20 24 2 0 0 0 0 20 28 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 25 37 2 0 0 0 0 25 42 1 0 0 0 0 26 38 2 0 0 0 0 26 43 1 0 0 0 0 27 39 2 0 0 0 0 27 44 1 0 0 0 0 28 15 1 6 0 0 0 28 42 1 0 0 0 0 29 21 1 1 0 0 0 29 34 1 0 0 0 0 30 21 1 6 0 0 0 30 43 1 0 0 0 0 31 35 1 0 0 0 0 31 36 1 1 0 0 0 32 34 1 0 0 0 0 32 40 2 0 0 0 0 33 35 1 0 0 0 0 33 41 1 1 0 0 0 36 11 1 1 0 0 0 36 44 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.4
Volume:	665.966
LogP:	5.69
LogD:	3.748
LogS:	-4.635
# Rotatable Bonds:	15
TPSA:	116.2
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.142
Synthetic Accessibility Score:	5.259
Fsp3:	0.722
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-4.786
MDCK Permeability:	5.101656643091701e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.719
20% Bioavailability (F20%):	0.834
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167
Plasma Protein Binding (PPB):	82.69402313232422%
Volume Distribution (VD):	1.458
Pgp-substrate:	7.287744998931885%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.446
CYP2C9-inhibitor:	0.276
CYP2C9-substrate:	0.175
CYP2D6-inhibitor:	0.042
CYP2D6-substrate:	0.121
CYP3A4-inhibitor:	0.486
CYP3A4-substrate:	0.588

ADMET: Excretion

Clearance (CL):	5.279
Half-life (T1/2):	0.192

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.951
Drug-inuced Liver Injury (DILI):	0.542
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.443
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.388
Carcinogencity:	0.061
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC285513

Natural Product ID:	NPC285513
*Common Name:**	Pouogenin B
IUPAC Name:	[(2S,3E,5R,7E)-2-acetyloxy-10-[(1S,3S,6S)-6-acetyloxy-3-hydroxy-2,2,6-trimethylcyclohexyl]-3,8-dimethyl-1-[(1R)-2,6,6-trimethyl-5-oxocyclohex-2-en-1-yl]deca-3,7-dien-5-yl] acetate
Synonyms:	Pouogenin B
Standard InCHIKey:	LOUNPPZOBFGBQD-MQQGKSLRSA-N
Standard InCHI:	InChI=1S/C36H56O8/c1-22(13-16-31-35(9,10)33(41)18-19-36(31,11)44-27(6)39)12-15-28(42-25(4)37)20-24(3)30(43-26(5)38)21-29-23(2)14-17-32(40)34(29,7)8/h12,14,20,28-31,33,41H,13,15-19,21H2,1-11H3/b22-12+,24-20+/t28-,29-,30+,31+,33+,36+/m1/s1
SMILES:	C/C(=CC[C@H](/C=C(C)/[C@H](C[C@@H]1C(=CCC(=O)C1(C)C)C)OC(=O)C)OC(=O)C)/CC[C@H]1C(C)(C)[C@H](CC[C@]1(C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1927959
PubChem CID:	56926500
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
NPO33227	Lipastrotethya sp.	Species	n.a.	n.a.	n.a.	Micronesia	n.a.	PMID[22148280]
NPO30078	Lipastrotethya	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22148280]
NPO33227	Lipastrotethya sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22742761]
NPO33227	Lipastrotethya sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[27779395]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	38900.0	nM	PMID[492923]

☑ 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 NPC285513 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	203
0.1-0.2	1182
0.2-0.3	3978
0.3-0.4	7389
0.4-0.5	14175
0.5-0.6	7071
0.6-0.7	6101
0.7-0.8	2491
0.8-0.85	100
0.85-0.9	3
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.978	High Similarity	NPC254496
0.956	High Similarity	NPC134067
0.9375	High Similarity	NPC118911
0.8673	High Similarity	NPC115862
0.8654	High Similarity	NPC311592
0.8654	High Similarity	NPC75167
0.8571	High Similarity	NPC181145
0.85	High Similarity	NPC90177
0.8478	Intermediate Similarity	NPC473226
0.8421	Intermediate Similarity	NPC472975
0.84	Intermediate Similarity	NPC162973
0.84	Intermediate Similarity	NPC474709
0.84	Intermediate Similarity	NPC136289
0.8387	Intermediate Similarity	NPC231599
0.8384	Intermediate Similarity	NPC474718
0.8384	Intermediate Similarity	NPC472644
0.8381	Intermediate Similarity	NPC174836
0.8367	Intermediate Similarity	NPC474977
0.8367	Intermediate Similarity	NPC474343
0.8365	Intermediate Similarity	NPC83005
0.8351	Intermediate Similarity	NPC266899
0.8351	Intermediate Similarity	NPC316215
0.8351	Intermediate Similarity	NPC477437
0.8351	Intermediate Similarity	NPC477438
0.835	Intermediate Similarity	NPC476479
0.8333	Intermediate Similarity	NPC477436
0.8333	Intermediate Similarity	NPC472645
0.8333	Intermediate Similarity	NPC477435
0.8317	Intermediate Similarity	NPC194323
0.83	Intermediate Similarity	NPC81530
0.83	Intermediate Similarity	NPC472643
0.83	Intermediate Similarity	NPC471412
0.8283	Intermediate Similarity	NPC58942
0.8283	Intermediate Similarity	NPC260149
0.8283	Intermediate Similarity	NPC316598
0.828	Intermediate Similarity	NPC220478
0.828	Intermediate Similarity	NPC325594
0.828	Intermediate Similarity	NPC73038
0.8265	Intermediate Similarity	NPC327179
0.8252	Intermediate Similarity	NPC475294
0.8247	Intermediate Similarity	NPC476415
0.8247	Intermediate Similarity	NPC470957
0.8247	Intermediate Similarity	NPC250075
0.8247	Intermediate Similarity	NPC91010
0.8247	Intermediate Similarity	NPC477439
0.8247	Intermediate Similarity	NPC470958
0.8229	Intermediate Similarity	NPC475972
0.8229	Intermediate Similarity	NPC233345
0.8229	Intermediate Similarity	NPC186363
0.8218	Intermediate Similarity	NPC32577
0.8218	Intermediate Similarity	NPC155332
0.8218	Intermediate Similarity	NPC476081
0.8218	Intermediate Similarity	NPC114540
0.82	Intermediate Similarity	NPC117685
0.82	Intermediate Similarity	NPC471413
0.82	Intermediate Similarity	NPC476274
0.8182	Intermediate Similarity	NPC38530
0.8182	Intermediate Similarity	NPC69385
0.8182	Intermediate Similarity	NPC84335
0.8182	Intermediate Similarity	NPC253826
0.8182	Intermediate Similarity	NPC48692
0.8173	Intermediate Similarity	NPC189075
0.8173	Intermediate Similarity	NPC275539
0.8163	Intermediate Similarity	NPC183012
0.8163	Intermediate Similarity	NPC53565
0.8155	Intermediate Similarity	NPC475414
0.8155	Intermediate Similarity	NPC127609
0.8155	Intermediate Similarity	NPC469607
0.8155	Intermediate Similarity	NPC111952
0.8155	Intermediate Similarity	NPC173172
0.8155	Intermediate Similarity	NPC284365
0.8155	Intermediate Similarity	NPC123726
0.8144	Intermediate Similarity	NPC139692
0.8144	Intermediate Similarity	NPC169343
0.8137	Intermediate Similarity	NPC8196
0.8132	Intermediate Similarity	NPC327002
0.8132	Intermediate Similarity	NPC229584
0.8132	Intermediate Similarity	NPC14203
0.8132	Intermediate Similarity	NPC473420
0.8131	Intermediate Similarity	NPC471204
0.8131	Intermediate Similarity	NPC25909
0.8125	Intermediate Similarity	NPC232202
0.8125	Intermediate Similarity	NPC134321
0.8125	Intermediate Similarity	NPC128672
0.8119	Intermediate Similarity	NPC224720
0.8119	Intermediate Similarity	NPC476240
0.8119	Intermediate Similarity	NPC476223
0.8119	Intermediate Similarity	NPC472637
0.8105	Intermediate Similarity	NPC24816
0.8105	Intermediate Similarity	NPC477128
0.81	Intermediate Similarity	NPC478056
0.81	Intermediate Similarity	NPC222011
0.8095	Intermediate Similarity	NPC472216
0.8095	Intermediate Similarity	NPC284828
0.8095	Intermediate Similarity	NPC173905
0.8095	Intermediate Similarity	NPC5475
0.8085	Intermediate Similarity	NPC202394
0.8085	Intermediate Similarity	NPC6979
0.8085	Intermediate Similarity	NPC250981
0.8085	Intermediate Similarity	NPC322159
0.8081	Intermediate Similarity	NPC202833
0.8077	Intermediate Similarity	NPC475176
0.8077	Intermediate Similarity	NPC112780
0.8077	Intermediate Similarity	NPC110496
0.8077	Intermediate Similarity	NPC143609
0.8065	Intermediate Similarity	NPC40687
0.8061	Intermediate Similarity	NPC472977
0.8061	Intermediate Similarity	NPC38830
0.8061	Intermediate Similarity	NPC472976
0.8058	Intermediate Similarity	NPC239162
0.8041	Intermediate Similarity	NPC26888
0.8041	Intermediate Similarity	NPC470590
0.8041	Intermediate Similarity	NPC472978
0.8041	Intermediate Similarity	NPC477574
0.8041	Intermediate Similarity	NPC285184
0.8041	Intermediate Similarity	NPC77099
0.8041	Intermediate Similarity	NPC60755
0.8039	Intermediate Similarity	NPC308726
0.8039	Intermediate Similarity	NPC119601
0.8039	Intermediate Similarity	NPC476890
0.8039	Intermediate Similarity	NPC478156
0.8039	Intermediate Similarity	NPC137430
0.8039	Intermediate Similarity	NPC185530
0.8037	Intermediate Similarity	NPC277769
0.8037	Intermediate Similarity	NPC475524
0.8037	Intermediate Similarity	NPC100267
0.8021	Intermediate Similarity	NPC5509
0.8021	Intermediate Similarity	NPC284561
0.8021	Intermediate Similarity	NPC472973
0.802	Intermediate Similarity	NPC476299
0.802	Intermediate Similarity	NPC266955
0.802	Intermediate Similarity	NPC472972
0.802	Intermediate Similarity	NPC474012
0.8019	Intermediate Similarity	NPC472215
0.8019	Intermediate Similarity	NPC475563
0.8019	Intermediate Similarity	NPC475134
0.8019	Intermediate Similarity	NPC472214
0.8	Intermediate Similarity	NPC476802
0.8	Intermediate Similarity	NPC311554
0.8	Intermediate Similarity	NPC175351
0.8	Intermediate Similarity	NPC151681
0.8	Intermediate Similarity	NPC477926
0.8	Intermediate Similarity	NPC189880
0.8	Intermediate Similarity	NPC132753
0.8	Intermediate Similarity	NPC170131
0.8	Intermediate Similarity	NPC257457
0.8	Intermediate Similarity	NPC151393
0.8	Intermediate Similarity	NPC121402
0.8	Intermediate Similarity	NPC224356
0.8	Intermediate Similarity	NPC89171
0.7981	Intermediate Similarity	NPC478052
0.7981	Intermediate Similarity	NPC278628
0.7981	Intermediate Similarity	NPC1679
0.7981	Intermediate Similarity	NPC231530
0.798	Intermediate Similarity	NPC473240
0.798	Intermediate Similarity	NPC37603
0.798	Intermediate Similarity	NPC471786
0.798	Intermediate Similarity	NPC317586
0.798	Intermediate Similarity	NPC139570
0.798	Intermediate Similarity	NPC470016
0.7979	Intermediate Similarity	NPC35933
0.7979	Intermediate Similarity	NPC52628
0.7961	Intermediate Similarity	NPC471364
0.7961	Intermediate Similarity	NPC36688
0.7961	Intermediate Similarity	NPC476889
0.7961	Intermediate Similarity	NPC132395
0.7961	Intermediate Similarity	NPC99266
0.7961	Intermediate Similarity	NPC26478
0.7961	Intermediate Similarity	NPC471365
0.7961	Intermediate Similarity	NPC120321
0.7959	Intermediate Similarity	NPC476416
0.7959	Intermediate Similarity	NPC158059
0.7959	Intermediate Similarity	NPC99653
0.7959	Intermediate Similarity	NPC202728
0.7959	Intermediate Similarity	NPC86368
0.7959	Intermediate Similarity	NPC118519
0.7957	Intermediate Similarity	NPC470948
0.7957	Intermediate Similarity	NPC222358
0.7957	Intermediate Similarity	NPC105173
0.7944	Intermediate Similarity	NPC475668
0.7944	Intermediate Similarity	NPC473921
0.7944	Intermediate Similarity	NPC475480
0.7941	Intermediate Similarity	NPC115899
0.7941	Intermediate Similarity	NPC163372
0.7941	Intermediate Similarity	NPC233012
0.7941	Intermediate Similarity	NPC303559
0.7941	Intermediate Similarity	NPC93744
0.7941	Intermediate Similarity	NPC474327
0.7941	Intermediate Similarity	NPC235142
0.7941	Intermediate Similarity	NPC302537
0.7941	Intermediate Similarity	NPC54909
0.7941	Intermediate Similarity	NPC476888
0.7938	Intermediate Similarity	NPC476369
0.7938	Intermediate Similarity	NPC476437
0.7938	Intermediate Similarity	NPC111585
0.7938	Intermediate Similarity	NPC198818
0.7938	Intermediate Similarity	NPC474728
0.7938	Intermediate Similarity	NPC120840
0.7938	Intermediate Similarity	NPC113989
0.7938	Intermediate Similarity	NPC471896

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 NPC285513 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	176
0.1-0.2	1592
0.2-0.3	3496
0.3-0.4	2400
0.4-0.5	958
0.5-0.6	286
0.6-0.7	191
0.7-0.8	51
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7879	Intermediate Similarity	NPD7748	Approved
0.7822	Intermediate Similarity	NPD7902	Approved
0.781	Intermediate Similarity	NPD5739	Approved
0.781	Intermediate Similarity	NPD6675	Approved
0.781	Intermediate Similarity	NPD6402	Approved
0.781	Intermediate Similarity	NPD7128	Approved
0.7778	Intermediate Similarity	NPD6399	Phase 3
0.7757	Intermediate Similarity	NPD6372	Approved
0.7757	Intermediate Similarity	NPD6373	Approved
0.7706	Intermediate Similarity	NPD8297	Approved
0.7677	Intermediate Similarity	NPD7515	Phase 2
0.7677	Intermediate Similarity	NPD6411	Approved
0.7664	Intermediate Similarity	NPD6881	Approved
0.7664	Intermediate Similarity	NPD7320	Approved
0.7664	Intermediate Similarity	NPD6899	Approved
0.7615	Intermediate Similarity	NPD6649	Approved
0.7615	Intermediate Similarity	NPD8130	Phase 1
0.7615	Intermediate Similarity	NPD6650	Approved
0.76	Intermediate Similarity	NPD5779	Approved
0.76	Intermediate Similarity	NPD5778	Approved
0.7573	Intermediate Similarity	NPD7638	Approved
0.757	Intermediate Similarity	NPD5697	Approved
0.757	Intermediate Similarity	NPD5701	Approved
0.7545	Intermediate Similarity	NPD6882	Approved
0.7525	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD7900	Approved
0.7523	Intermediate Similarity	NPD7102	Approved
0.7523	Intermediate Similarity	NPD7290	Approved
0.7523	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD6011	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.7475	Intermediate Similarity	NPD6101	Approved
0.7475	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD5328	Approved
0.7455	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6617	Approved
0.7455	Intermediate Similarity	NPD6869	Approved
0.7455	Intermediate Similarity	NPD6847	Approved
0.7434	Intermediate Similarity	NPD7115	Discovery
0.7431	Intermediate Similarity	NPD6013	Approved
0.7431	Intermediate Similarity	NPD6014	Approved
0.7431	Intermediate Similarity	NPD6012	Approved
0.7404	Intermediate Similarity	NPD4225	Approved
0.7339	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD6079	Approved
0.732	Intermediate Similarity	NPD4786	Approved
0.7308	Intermediate Similarity	NPD4755	Approved
0.7292	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD3667	Approved
0.7273	Intermediate Similarity	NPD3573	Approved
0.7273	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD1694	Approved
0.7207	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD5211	Phase 2
0.7182	Intermediate Similarity	NPD6686	Approved
0.7172	Intermediate Similarity	NPD3618	Phase 1
0.717	Intermediate Similarity	NPD4696	Approved
0.717	Intermediate Similarity	NPD5286	Approved
0.717	Intermediate Similarity	NPD4700	Approved
0.717	Intermediate Similarity	NPD5285	Approved
0.7157	Intermediate Similarity	NPD8034	Phase 2
0.7157	Intermediate Similarity	NPD8035	Phase 2
0.7156	Intermediate Similarity	NPD6008	Approved
0.7143	Intermediate Similarity	NPD6083	Phase 2
0.7143	Intermediate Similarity	NPD6084	Phase 2
0.7115	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD5223	Approved
0.7097	Intermediate Similarity	NPD8039	Approved
0.7087	Intermediate Similarity	NPD4202	Approved
0.7083	Intermediate Similarity	NPD7507	Approved
0.708	Intermediate Similarity	NPD6053	Discontinued
0.7069	Intermediate Similarity	NPD6335	Approved
0.7064	Intermediate Similarity	NPD5141	Approved
0.7059	Intermediate Similarity	NPD46	Approved
0.7059	Intermediate Similarity	NPD6698	Approved
0.7048	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5222	Approved
0.7048	Intermediate Similarity	NPD5221	Approved
0.7048	Intermediate Similarity	NPD4697	Phase 3
0.7043	Intermediate Similarity	NPD6274	Approved
0.7037	Intermediate Similarity	NPD5224	Approved
0.7037	Intermediate Similarity	NPD5225	Approved
0.7037	Intermediate Similarity	NPD5226	Approved
0.7037	Intermediate Similarity	NPD4633	Approved
0.7018	Intermediate Similarity	NPD4632	Approved
0.7009	Intermediate Similarity	NPD7101	Approved
0.7009	Intermediate Similarity	NPD7100	Approved
0.7	Intermediate Similarity	NPD4767	Approved
0.7	Intermediate Similarity	NPD7521	Approved
0.7	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD4768	Approved
0.7	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD5330	Approved
0.7	Intermediate Similarity	NPD6409	Approved
0.7	Intermediate Similarity	NPD7334	Approved
0.699	Remote Similarity	NPD7983	Approved
0.6983	Remote Similarity	NPD6317	Approved
0.6981	Remote Similarity	NPD5173	Approved
0.6972	Remote Similarity	NPD4754	Approved
0.6972	Remote Similarity	NPD5174	Approved
0.6972	Remote Similarity	NPD5175	Approved
0.6964	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD5695	Phase 3
0.6949	Remote Similarity	NPD6319	Approved
0.6944	Remote Similarity	NPD5344	Discontinued
0.6939	Remote Similarity	NPD6435	Approved
0.6937	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6314	Approved
0.6923	Remote Similarity	NPD6313	Approved
0.6917	Remote Similarity	NPD8328	Phase 3
0.6911	Remote Similarity	NPD7319	Approved
0.69	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6868	Approved
0.6893	Remote Similarity	NPD5785	Approved
0.6891	Remote Similarity	NPD8513	Phase 3
0.6891	Remote Similarity	NPD8515	Approved
0.6891	Remote Similarity	NPD8517	Approved
0.6891	Remote Similarity	NPD8516	Approved
0.6891	Remote Similarity	NPD6908	Approved
0.6891	Remote Similarity	NPD6909	Approved
0.6881	Remote Similarity	NPD7632	Discontinued
0.6875	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD4730	Approved
0.6875	Remote Similarity	NPD4729	Approved
0.6863	Remote Similarity	NPD5737	Approved
0.6863	Remote Similarity	NPD6903	Approved
0.6863	Remote Similarity	NPD6672	Approved
0.6863	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6009	Approved
0.6832	Remote Similarity	NPD5786	Approved
0.6827	Remote Similarity	NPD5693	Phase 1
0.68	Remote Similarity	NPD3666	Approved
0.68	Remote Similarity	NPD3665	Phase 1
0.68	Remote Similarity	NPD3133	Approved
0.68	Remote Similarity	NPD3668	Phase 3
0.6796	Remote Similarity	NPD6051	Approved
0.6792	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD7604	Phase 2
0.6759	Remote Similarity	NPD5696	Approved
0.6754	Remote Similarity	NPD5249	Phase 3
0.6754	Remote Similarity	NPD5247	Approved
0.6754	Remote Similarity	NPD5250	Approved
0.6754	Remote Similarity	NPD5251	Approved
0.6754	Remote Similarity	NPD5248	Approved
0.675	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5983	Phase 2
0.675	Remote Similarity	NPD6921	Approved
0.6748	Remote Similarity	NPD8293	Discontinued
0.6737	Remote Similarity	NPD8264	Approved
0.6735	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4695	Discontinued
0.6735	Remote Similarity	NPD7525	Registered
0.6735	Remote Similarity	NPD5368	Approved
0.6729	Remote Similarity	NPD7839	Suspended
0.6726	Remote Similarity	NPD5128	Approved
0.6724	Remote Similarity	NPD8133	Approved
0.6721	Remote Similarity	NPD7492	Approved
0.67	Remote Similarity	NPD5362	Discontinued
0.67	Remote Similarity	NPD7154	Phase 3
0.6697	Remote Similarity	NPD6648	Approved
0.6694	Remote Similarity	NPD7736	Approved
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD6422	Discontinued
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD5369	Approved
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD6059	Approved
0.6667	Remote Similarity	NPD7637	Suspended
0.6639	Remote Similarity	NPD7327	Approved
0.6639	Remote Similarity	NPD7328	Approved
0.6635	Remote Similarity	NPD6080	Approved
0.6635	Remote Similarity	NPD4753	Phase 2
0.6635	Remote Similarity	NPD6904	Approved
0.6635	Remote Similarity	NPD6673	Approved
0.6635	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD7645	Phase 2
0.6613	Remote Similarity	NPD7078	Approved
0.6613	Remote Similarity	NPD8074	Phase 3
0.6612	Remote Similarity	NPD8033	Approved
0.6609	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD5169	Approved
0.6609	Remote Similarity	NPD6371	Approved
0.6609	Remote Similarity	NPD5135	Approved
0.6609	Remote Similarity	NPD4634	Approved
0.6606	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4269	Approved
0.66	Remote Similarity	NPD4270	Approved
0.6583	Remote Similarity	NPD7516	Approved
0.6571	Remote Similarity	NPD7838	Discovery
0.6569	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4821	Approved
0.6566	Remote Similarity	NPD4822	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