NPASS Compound

Structure

NPC232202 OpenBabel07101719512D 27 28 0 0 1 0 0 0 0 0999 V2000 0.8660 -3.5000 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 2.3660 4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 2.3660 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 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 -0.8660 -3.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 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 2.8660 3.2321 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 -0.5000 0.0000 C 0 0 1 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 0.0000 1.0000 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 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 3.2321 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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3660 2.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 2 0 0 0 0 3 16 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 9 23 1 0 0 0 0 10 19 1 0 0 0 0 10 20 1 0 0 0 0 11 17 1 0 0 0 0 11 21 1 0 0 0 0 12 17 1 0 0 0 0 12 22 1 0 0 0 0 13 21 1 0 0 0 0 13 27 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 24 2 0 0 0 0 16 27 1 0 0 0 0 17 25 2 0 0 0 0 18 22 1 1 0 0 0 19 26 1 6 0 0 0 20 21 1 1 0 0 0 20 22 1 0 0 0 0 21 4 1 6 0 0 0 22 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.24
Volume:	405.361
LogP:	1.175
LogD:	1.628
LogS:	-3.031
# Rotatable Bonds:	7
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.548
Synthetic Accessibility Score:	4.751
Fsp3:	0.727
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.117
MDCK Permeability:	9.695332664705347e-06
Pgp-inhibitor:	0.017
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.927
30% Bioavailability (F30%):	0.08

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.413
Plasma Protein Binding (PPB):	60.9422607421875%
Volume Distribution (VD):	0.666
Pgp-substrate:	37.64348220825195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.627
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.089
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.456
CYP3A4-substrate:	0.272

ADMET: Excretion

Clearance (CL):	2.541
Half-life (T1/2):	0.853

ADMET: Toxicity

hERG Blockers:	0.02
Human Hepatotoxicity (H-HT):	0.406
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.068
Maximum Recommended Daily Dose:	0.869
Skin Sensitization:	0.204
Carcinogencity:	0.072
Eye Corrosion:	0.034
Eye Irritation:	0.384
Respiratory Toxicity:	0.909

Download Data

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

Natural Product: NPC232202

Natural Product ID:	NPC232202
*Common Name:**	19-Acetoxy-7Alpha,15-Dihydroxylabda-8(17),(13Z)-Dien-2-One
IUPAC Name:	[(1S,4aS,5R,7R,8aR)-7-hydroxy-5-[(Z)-5-hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3-oxo-2,4,5,7,8,8a-hexahydronaphthalen-1-yl]methyl acetate
Synonyms:
Standard InCHIKey:	AHIPHYZNSMHQBT-ITOMHQBLSA-N
Standard InCHI:	InChI=1S/C22H34O5/c1-14(8-9-23)6-7-18-15(2)19(26)10-20-21(4,13-27-16(3)24)11-17(25)12-22(18,20)5/h8,18-20,23,26H,2,6-7,9-13H2,1,3-5H3/b14-8-/t18-,19+,20-,21+,22+/m0/s1
SMILES:	C/C(=C/CO)/CC[C@H]1C(=C)[C@@H](C[C@H]2[C@](C)(CC(=O)C[C@]12C)COC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453006
PubChem CID:	21672196
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO3153	Hyptis spicigera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917280]
NPO3153	Hyptis spicigera	Species	Lamiaceae	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	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	11.0	ug ml-1	PMID[566404]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	11.0	ug ml-1	PMID[566404]

☑ 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 NPC232202 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	193
0.1-0.2	1085
0.2-0.3	3826
0.3-0.4	7366
0.4-0.5	14284
0.5-0.6	6570
0.6-0.7	5917
0.7-0.8	3262
0.8-0.85	170
0.85-0.9	22
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9059	High Similarity	NPC102048
0.8842	High Similarity	NPC478057
0.8778	High Similarity	NPC198054
0.8652	High Similarity	NPC104560
0.8646	High Similarity	NPC95899
0.8636	High Similarity	NPC202394
0.8636	High Similarity	NPC322159
0.8632	High Similarity	NPC97435
0.8617	High Similarity	NPC478056
0.8602	High Similarity	NPC134072
0.8602	High Similarity	NPC234993
0.8602	High Similarity	NPC202833
0.8587	High Similarity	NPC470958
0.8587	High Similarity	NPC470957
0.8571	High Similarity	NPC239098
0.8542	High Similarity	NPC137430
0.8523	High Similarity	NPC52628
0.8511	High Similarity	NPC474343
0.8495	Intermediate Similarity	NPC266899
0.8495	Intermediate Similarity	NPC474727
0.8495	Intermediate Similarity	NPC134067
0.8488	Intermediate Similarity	NPC14203
0.8488	Intermediate Similarity	NPC229584
0.8478	Intermediate Similarity	NPC199543
0.8462	Intermediate Similarity	NPC48732
0.8454	Intermediate Similarity	NPC99266
0.8454	Intermediate Similarity	NPC8196
0.8444	Intermediate Similarity	NPC291665
0.8438	Intermediate Similarity	NPC471412
0.8427	Intermediate Similarity	NPC329692
0.8427	Intermediate Similarity	NPC73038
0.8427	Intermediate Similarity	NPC472985
0.8427	Intermediate Similarity	NPC325594
0.8427	Intermediate Similarity	NPC472986
0.8427	Intermediate Similarity	NPC473226
0.8387	Intermediate Similarity	NPC250075
0.8387	Intermediate Similarity	NPC57117
0.8384	Intermediate Similarity	NPC230541
0.8372	Intermediate Similarity	NPC469802
0.8352	Intermediate Similarity	NPC281524
0.8351	Intermediate Similarity	NPC476081
0.8351	Intermediate Similarity	NPC136289
0.8333	Intermediate Similarity	NPC218383
0.8333	Intermediate Similarity	NPC266955
0.8333	Intermediate Similarity	NPC251680
0.8333	Intermediate Similarity	NPC477926
0.8333	Intermediate Similarity	NPC471413
0.8333	Intermediate Similarity	NPC476274
0.8333	Intermediate Similarity	NPC476767
0.8333	Intermediate Similarity	NPC306856
0.8333	Intermediate Similarity	NPC471041
0.8316	Intermediate Similarity	NPC254496
0.8316	Intermediate Similarity	NPC475894
0.8316	Intermediate Similarity	NPC253826
0.8316	Intermediate Similarity	NPC476878
0.8316	Intermediate Similarity	NPC476879
0.8298	Intermediate Similarity	NPC53565
0.8298	Intermediate Similarity	NPC279974
0.8295	Intermediate Similarity	NPC105173
0.8295	Intermediate Similarity	NPC312480
0.8283	Intermediate Similarity	NPC127609
0.828	Intermediate Similarity	NPC107674
0.828	Intermediate Similarity	NPC139692
0.828	Intermediate Similarity	NPC99653
0.828	Intermediate Similarity	NPC170220
0.828	Intermediate Similarity	NPC476416
0.828	Intermediate Similarity	NPC141497
0.8276	Intermediate Similarity	NPC170303
0.8265	Intermediate Similarity	NPC36688
0.8265	Intermediate Similarity	NPC120321
0.8265	Intermediate Similarity	NPC95585
0.8265	Intermediate Similarity	NPC282233
0.8261	Intermediate Similarity	NPC158488
0.8261	Intermediate Similarity	NPC291028
0.8247	Intermediate Similarity	NPC81530
0.8247	Intermediate Similarity	NPC224720
0.8247	Intermediate Similarity	NPC115862
0.8247	Intermediate Similarity	NPC115899
0.8247	Intermediate Similarity	NPC303559
0.8247	Intermediate Similarity	NPC476223
0.8247	Intermediate Similarity	NPC476240
0.8229	Intermediate Similarity	NPC119036
0.8222	Intermediate Similarity	NPC82979
0.8222	Intermediate Similarity	NPC198761
0.8218	Intermediate Similarity	NPC141350
0.8211	Intermediate Similarity	NPC301534
0.8211	Intermediate Similarity	NPC242848
0.8211	Intermediate Similarity	NPC7124
0.8211	Intermediate Similarity	NPC250757
0.8202	Intermediate Similarity	NPC97505
0.82	Intermediate Similarity	NPC143609
0.82	Intermediate Similarity	NPC187435
0.82	Intermediate Similarity	NPC67321
0.8191	Intermediate Similarity	NPC91010
0.8191	Intermediate Similarity	NPC159410
0.8172	Intermediate Similarity	NPC110657
0.8172	Intermediate Similarity	NPC297265
0.8172	Intermediate Similarity	NPC477574
0.8172	Intermediate Similarity	NPC473944
0.8172	Intermediate Similarity	NPC212301
0.8172	Intermediate Similarity	NPC105189
0.8172	Intermediate Similarity	NPC124374
0.8172	Intermediate Similarity	NPC86266
0.8172	Intermediate Similarity	NPC476417
0.8163	Intermediate Similarity	NPC234892
0.8163	Intermediate Similarity	NPC469606
0.8163	Intermediate Similarity	NPC273005
0.8163	Intermediate Similarity	NPC293753
0.8163	Intermediate Similarity	NPC31058
0.8163	Intermediate Similarity	NPC162973
0.8161	Intermediate Similarity	NPC281880
0.8152	Intermediate Similarity	NPC194642
0.8152	Intermediate Similarity	NPC246028
0.8152	Intermediate Similarity	NPC16265
0.8152	Intermediate Similarity	NPC50488
0.8152	Intermediate Similarity	NPC474396
0.8144	Intermediate Similarity	NPC307954
0.8144	Intermediate Similarity	NPC470074
0.8144	Intermediate Similarity	NPC477521
0.8144	Intermediate Similarity	NPC47024
0.8144	Intermediate Similarity	NPC474718
0.8125	Intermediate Similarity	NPC189880
0.8125	Intermediate Similarity	NPC285513
0.8125	Intermediate Similarity	NPC320306
0.8125	Intermediate Similarity	NPC170131
0.8125	Intermediate Similarity	NPC107243
0.8125	Intermediate Similarity	NPC272451
0.8125	Intermediate Similarity	NPC472851
0.8119	Intermediate Similarity	NPC151393
0.8119	Intermediate Similarity	NPC472219
0.8119	Intermediate Similarity	NPC472217
0.8119	Intermediate Similarity	NPC322903
0.8119	Intermediate Similarity	NPC102843
0.8119	Intermediate Similarity	NPC189075
0.8119	Intermediate Similarity	NPC472218
0.8119	Intermediate Similarity	NPC275539
0.8119	Intermediate Similarity	NPC306265
0.8111	Intermediate Similarity	NPC476602
0.8111	Intermediate Similarity	NPC329738
0.8105	Intermediate Similarity	NPC469599
0.8105	Intermediate Similarity	NPC272617
0.8105	Intermediate Similarity	NPC290481
0.8105	Intermediate Similarity	NPC271195
0.8105	Intermediate Similarity	NPC139459
0.81	Intermediate Similarity	NPC111952
0.81	Intermediate Similarity	NPC34768
0.81	Intermediate Similarity	NPC80566
0.8095	Intermediate Similarity	NPC306727
0.809	Intermediate Similarity	NPC476927
0.809	Intermediate Similarity	NPC470948
0.8085	Intermediate Similarity	NPC86368
0.8085	Intermediate Similarity	NPC474436
0.8085	Intermediate Similarity	NPC63118
0.8085	Intermediate Similarity	NPC169343
0.8085	Intermediate Similarity	NPC272075
0.8085	Intermediate Similarity	NPC147272
0.8085	Intermediate Similarity	NPC470224
0.8085	Intermediate Similarity	NPC49776
0.8085	Intermediate Similarity	NPC295643
0.8085	Intermediate Similarity	NPC214756
0.8081	Intermediate Similarity	NPC90177
0.8081	Intermediate Similarity	NPC140723
0.8081	Intermediate Similarity	NPC275583
0.8081	Intermediate Similarity	NPC222153
0.8081	Intermediate Similarity	NPC476237
0.8077	Intermediate Similarity	NPC962
0.8068	Intermediate Similarity	NPC159148
0.8068	Intermediate Similarity	NPC327002
0.8068	Intermediate Similarity	NPC473420
0.8068	Intermediate Similarity	NPC40228
0.8065	Intermediate Similarity	NPC210037
0.8065	Intermediate Similarity	NPC290614
0.8065	Intermediate Similarity	NPC7260
0.8065	Intermediate Similarity	NPC227467
0.8065	Intermediate Similarity	NPC198818
0.8065	Intermediate Similarity	NPC220216
0.8065	Intermediate Similarity	NPC273621
0.8065	Intermediate Similarity	NPC474728
0.8065	Intermediate Similarity	NPC46441
0.8065	Intermediate Similarity	NPC120840
0.8065	Intermediate Similarity	NPC193750
0.8065	Intermediate Similarity	NPC18872
0.8065	Intermediate Similarity	NPC51486
0.8065	Intermediate Similarity	NPC113989
0.8065	Intermediate Similarity	NPC120968
0.8065	Intermediate Similarity	NPC153853
0.8065	Intermediate Similarity	NPC471896
0.8065	Intermediate Similarity	NPC477872
0.8061	Intermediate Similarity	NPC477051
0.8061	Intermediate Similarity	NPC477052
0.8061	Intermediate Similarity	NPC253886
0.8061	Intermediate Similarity	NPC121218
0.8061	Intermediate Similarity	NPC477053
0.8046	Intermediate Similarity	NPC308038
0.8046	Intermediate Similarity	NPC327674
0.8043	Intermediate Similarity	NPC182797
0.8043	Intermediate Similarity	NPC40552
0.8043	Intermediate Similarity	NPC246708
0.8043	Intermediate Similarity	NPC48107
0.8043	Intermediate Similarity	NPC52169

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 NPC232202 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	1434
0.2-0.3	3534
0.3-0.4	2466
0.4-0.5	1005
0.5-0.6	232
0.6-0.7	245
0.7-0.8	67
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8333	Intermediate Similarity	NPD7640	Approved
0.8333	Intermediate Similarity	NPD7639	Approved
0.8229	Intermediate Similarity	NPD7638	Approved
0.8085	Intermediate Similarity	NPD6399	Phase 3
0.8	Intermediate Similarity	NPD7748	Approved
0.7979	Intermediate Similarity	NPD7515	Phase 2
0.7938	Intermediate Similarity	NPD7902	Approved
0.7895	Intermediate Similarity	NPD5778	Approved
0.7895	Intermediate Similarity	NPD5779	Approved
0.7677	Intermediate Similarity	NPD4225	Approved
0.7634	Intermediate Similarity	NPD3618	Phase 1
0.7629	Intermediate Similarity	NPD7900	Approved
0.7629	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD7632	Discontinued
0.7609	Intermediate Similarity	NPD4786	Approved
0.7604	Intermediate Similarity	NPD7637	Suspended
0.7596	Intermediate Similarity	NPD6686	Approved
0.7582	Intermediate Similarity	NPD3667	Approved
0.7582	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6684	Approved
0.7447	Intermediate Similarity	NPD7334	Approved
0.7447	Intermediate Similarity	NPD7521	Approved
0.7447	Intermediate Similarity	NPD7146	Approved
0.7447	Intermediate Similarity	NPD6409	Approved
0.7447	Intermediate Similarity	NPD5330	Approved
0.7423	Intermediate Similarity	NPD6411	Approved
0.7423	Intermediate Similarity	NPD8035	Phase 2
0.7423	Intermediate Similarity	NPD8034	Phase 2
0.7404	Intermediate Similarity	NPD7128	Approved
0.7404	Intermediate Similarity	NPD6402	Approved
0.7404	Intermediate Similarity	NPD5739	Approved
0.7404	Intermediate Similarity	NPD6675	Approved
0.74	Intermediate Similarity	NPD6083	Phase 2
0.74	Intermediate Similarity	NPD6084	Phase 2
0.7396	Intermediate Similarity	NPD5328	Approved
0.7364	Intermediate Similarity	NPD7115	Discovery
0.7358	Intermediate Similarity	NPD6373	Approved
0.7358	Intermediate Similarity	NPD6372	Approved
0.7358	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6672	Approved
0.7292	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6903	Approved
0.7292	Intermediate Similarity	NPD5737	Approved
0.7264	Intermediate Similarity	NPD7320	Approved
0.7264	Intermediate Similarity	NPD6881	Approved
0.7264	Intermediate Similarity	NPD6899	Approved
0.7264	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD6079	Approved
0.7238	Intermediate Similarity	NPD6008	Approved
0.7234	Intermediate Similarity	NPD3666	Approved
0.7234	Intermediate Similarity	NPD3665	Phase 1
0.7234	Intermediate Similarity	NPD3133	Approved
0.7222	Intermediate Similarity	NPD6650	Approved
0.7222	Intermediate Similarity	NPD6649	Approved
0.7216	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6101	Approved
0.7204	Intermediate Similarity	NPD4269	Approved
0.7204	Intermediate Similarity	NPD4270	Approved
0.7196	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5697	Approved
0.717	Intermediate Similarity	NPD5701	Approved
0.717	Intermediate Similarity	NPD6412	Phase 2
0.7158	Intermediate Similarity	NPD1694	Approved
0.7157	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD46	Approved
0.7143	Intermediate Similarity	NPD6698	Approved
0.7143	Intermediate Similarity	NPD5785	Approved
0.713	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD6883	Approved
0.713	Intermediate Similarity	NPD7102	Approved
0.713	Intermediate Similarity	NPD7290	Approved
0.7129	Intermediate Similarity	NPD4697	Phase 3
0.7128	Intermediate Similarity	NPD6695	Phase 3
0.7128	Intermediate Similarity	NPD5362	Discontinued
0.7128	Intermediate Similarity	NPD7154	Phase 3
0.7103	Intermediate Similarity	NPD6011	Approved
0.7091	Intermediate Similarity	NPD4632	Approved
0.7083	Intermediate Similarity	NPD5786	Approved
0.7071	Intermediate Similarity	NPD7983	Approved
0.7064	Intermediate Similarity	NPD8130	Phase 1
0.7064	Intermediate Similarity	NPD6847	Approved
0.7064	Intermediate Similarity	NPD6869	Approved
0.7064	Intermediate Similarity	NPD6617	Approved
0.7064	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD3668	Phase 3
0.7053	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6013	Approved
0.7037	Intermediate Similarity	NPD6014	Approved
0.7037	Intermediate Similarity	NPD6012	Approved
0.703	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5695	Phase 3
0.701	Intermediate Similarity	NPD3573	Approved
0.7	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD8297	Approved
0.7	Intermediate Similarity	NPD4202	Approved
0.6989	Remote Similarity	NPD4695	Discontinued
0.6989	Remote Similarity	NPD4252	Approved
0.6983	Remote Similarity	NPD8328	Phase 3
0.6979	Remote Similarity	NPD5363	Approved
0.6972	Remote Similarity	NPD6371	Approved
0.6961	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD5222	Approved
0.6961	Remote Similarity	NPD5221	Approved
0.6957	Remote Similarity	NPD6118	Approved
0.6957	Remote Similarity	NPD6697	Approved
0.6957	Remote Similarity	NPD6114	Approved
0.6957	Remote Similarity	NPD6115	Approved
0.6952	Remote Similarity	NPD5211	Phase 2
0.6915	Remote Similarity	NPD5369	Approved
0.6907	Remote Similarity	NPD5279	Phase 3
0.6907	Remote Similarity	NPD6098	Approved
0.6907	Remote Similarity	NPD4623	Approved
0.6907	Remote Similarity	NPD4519	Discontinued
0.6903	Remote Similarity	NPD6009	Approved
0.6893	Remote Similarity	NPD5173	Approved
0.6893	Remote Similarity	NPD4755	Approved
0.6882	Remote Similarity	NPD7645	Phase 2
0.6882	Remote Similarity	NPD6929	Approved
0.687	Remote Similarity	NPD6319	Approved
0.6869	Remote Similarity	NPD6673	Approved
0.6869	Remote Similarity	NPD4753	Phase 2
0.6869	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6904	Approved
0.6869	Remote Similarity	NPD6080	Approved
0.6864	Remote Similarity	NPD7507	Approved
0.6857	Remote Similarity	NPD5344	Discontinued
0.6852	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6435	Approved
0.6838	Remote Similarity	NPD7604	Phase 2
0.6837	Remote Similarity	NPD4250	Approved
0.6837	Remote Similarity	NPD7750	Discontinued
0.6837	Remote Similarity	NPD7524	Approved
0.6837	Remote Similarity	NPD4251	Approved
0.6822	Remote Similarity	NPD5141	Approved
0.6814	Remote Similarity	NPD6868	Approved
0.6813	Remote Similarity	NPD8039	Approved
0.6813	Remote Similarity	NPD8264	Approved
0.681	Remote Similarity	NPD5983	Phase 2
0.6809	Remote Similarity	NPD7525	Registered
0.6809	Remote Similarity	NPD6930	Phase 2
0.6809	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6931	Approved
0.6796	Remote Similarity	NPD7839	Suspended
0.6786	Remote Similarity	NPD8133	Approved
0.678	Remote Similarity	NPD7492	Approved
0.6765	Remote Similarity	NPD5282	Discontinued
0.6762	Remote Similarity	NPD4700	Approved
0.6762	Remote Similarity	NPD5286	Approved
0.6762	Remote Similarity	NPD5285	Approved
0.6762	Remote Similarity	NPD4696	Approved
0.6754	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6117	Approved
0.6735	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4249	Approved
0.6733	Remote Similarity	NPD5693	Phase 1
0.6733	Remote Similarity	NPD5281	Approved
0.6733	Remote Similarity	NPD5284	Approved
0.6724	Remote Similarity	NPD6054	Approved
0.6724	Remote Similarity	NPD6059	Approved
0.6723	Remote Similarity	NPD6336	Discontinued
0.6723	Remote Similarity	NPD6616	Approved
0.6703	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6051	Approved
0.6699	Remote Similarity	NPD5210	Approved
0.6699	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4629	Approved
0.6698	Remote Similarity	NPD5223	Approved
0.6696	Remote Similarity	NPD6053	Discontinued
0.6696	Remote Similarity	NPD6335	Approved
0.6694	Remote Similarity	NPD7319	Approved
0.6667	Remote Similarity	NPD6925	Approved
0.6667	Remote Similarity	NPD5776	Phase 2
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6116	Phase 1
0.6667	Remote Similarity	NPD6274	Approved
0.6667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7078	Approved
0.6638	Remote Similarity	NPD7101	Approved
0.6638	Remote Similarity	NPD7100	Approved
0.6636	Remote Similarity	NPD4633	Approved
0.6636	Remote Similarity	NPD5224	Approved
0.6636	Remote Similarity	NPD5226	Approved
0.6636	Remote Similarity	NPD5225	Approved
0.6633	Remote Similarity	NPD5329	Approved
0.6633	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4819	Approved
0.6632	Remote Similarity	NPD4821	Approved
0.6632	Remote Similarity	NPD5368	Approved
0.6632	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7514	Phase 3
0.6632	Remote Similarity	NPD4820	Approved
0.6632	Remote Similarity	NPD4822	Approved
0.6632	Remote Similarity	NPD7332	Phase 2
0.663	Remote Similarity	NPD7339	Approved
0.663	Remote Similarity	NPD6942	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