NPASS Compound

Structure

CID1679 OpenBabel06191715322D 26 27 0 0 1 0 0 0 0 0999 V2000 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 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 0.8660 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 2.5981 -1.5000 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 -0.0000 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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 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 0.0000 -2.0000 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 -1.5000 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 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 17 1 0 0 0 0 8 13 2 0 0 0 0 8 14 1 0 0 0 0 9 13 1 0 0 0 0 9 20 2 0 0 0 0 10 19 1 0 0 0 0 10 21 2 0 0 0 0 11 22 2 0 0 0 0 11 25 1 0 0 0 0 12 23 2 0 0 0 0 12 26 1 0 0 0 0 13 19 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 1 0 0 0 15 18 1 6 0 0 0 15 26 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 6 0 0 0 18 19 1 1 0 0 0 19 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.17
Volume:	368.417
LogP:	1.591
LogD:	1.037
LogS:	-3.077
# Rotatable Bonds:	6
TPSA:	106.97
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.591
Synthetic Accessibility Score:	4.631
Fsp3:	0.684
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.054
MDCK Permeability:	0.00010805204510688782
Pgp-inhibitor:	0.157
Pgp-substrate:	0.089
Human Intestinal Absorption (HIA):	0.814
20% Bioavailability (F20%):	0.699
30% Bioavailability (F30%):	0.095

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.978
Plasma Protein Binding (PPB):	39.83671569824219%
Volume Distribution (VD):	1.592
Pgp-substrate:	64.14860534667969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.074
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.434
CYP3A4-substrate:	0.344

ADMET: Excretion

Clearance (CL):	2.397
Half-life (T1/2):	0.547

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.307
Drug-inuced Liver Injury (DILI):	0.107
AMES Toxicity:	0.949
Rat Oral Acute Toxicity:	0.828
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.962
Carcinogencity:	0.917
Eye Corrosion:	0.908
Eye Irritation:	0.504
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC1679

Natural Product ID:	NPC1679
*Common Name:**	Parritadial
IUPAC Name:	[(1R,4aS,5S,8S,8aR)-5-acetyloxy-7,8-diformyl-8-hydroxy-4,4,8a-trimethyl-2,3,4a,5-tetrahydro-1H-naphthalen-1-yl] acetate
Synonyms:	Parritadial
Standard InCHIKey:	WEBNABJUZWHBQV-JZFYCYHFSA-N
Standard InCHI:	InChI=1S/C19H26O7/c1-11(22)25-14-8-13(9-20)19(24,10-21)18(5)15(26-12(2)23)6-7-17(3,4)16(14)18/h8-10,14-16,24H,6-7H2,1-5H3/t14-,15+,16-,18-,19+/m0/s1
SMILES:	CC(=O)O[C@H]1C=C(C=O)[C@](C=O)([C@@]2(C)[C@@H](CCC(C)(C)[C@H]12)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526663
PubChem CID:	11844354
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000346] Dicarboxylic acids 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
NPO7432	Pleodendron costaricense	Species	Canellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16872133]
NPO4356	Eugenia wallichii	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO602	Kielmeyera lathrophyton	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12548	Jahnoporus hirtus	Species	Albatrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7432	Pleodendron costaricense	Species	Canellaceae	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
MIC	2
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	1000.0	ug.mL-1	PMID[495098]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	250.0	ug.mL-1	PMID[495098]
NPT20	Organism	Candida albicans	Candida albicans	FICI	=	1.5	n.a.	PMID[495098]

☑ 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 NPC1679 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	219
0.1-0.2	1280
0.2-0.3	4224
0.3-0.4	8042
0.4-0.5	12837
0.5-0.6	8370
0.6-0.7	5768
0.7-0.8	1895
0.8-0.85	53
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9485	High Similarity	NPC174314
0.8667	High Similarity	NPC89171
0.8667	High Similarity	NPC476802
0.8586	High Similarity	NPC470697
0.8571	High Similarity	NPC172101
0.8476	Intermediate Similarity	NPC472645
0.844	Intermediate Similarity	NPC56448
0.8431	Intermediate Similarity	NPC316598
0.8416	Intermediate Similarity	NPC242848
0.8411	Intermediate Similarity	NPC474243
0.8381	Intermediate Similarity	NPC470297
0.8381	Intermediate Similarity	NPC118911
0.835	Intermediate Similarity	NPC474012
0.835	Intermediate Similarity	NPC476299
0.8349	Intermediate Similarity	NPC476801
0.8349	Intermediate Similarity	NPC269530
0.8349	Intermediate Similarity	NPC90952
0.8333	Intermediate Similarity	NPC5103
0.8318	Intermediate Similarity	NPC322903
0.8317	Intermediate Similarity	NPC183012
0.8302	Intermediate Similarity	NPC477125
0.83	Intermediate Similarity	NPC115021
0.8273	Intermediate Similarity	NPC159333
0.8269	Intermediate Similarity	NPC472643
0.8257	Intermediate Similarity	NPC304180
0.8257	Intermediate Similarity	NPC179798
0.8218	Intermediate Similarity	NPC476415
0.8208	Intermediate Similarity	NPC146731
0.819	Intermediate Similarity	NPC80781
0.819	Intermediate Similarity	NPC162973
0.8182	Intermediate Similarity	NPC277769
0.8173	Intermediate Similarity	NPC475392
0.8173	Intermediate Similarity	NPC475385
0.8173	Intermediate Similarity	NPC472644
0.8173	Intermediate Similarity	NPC476274
0.8173	Intermediate Similarity	NPC117685
0.8173	Intermediate Similarity	NPC475202
0.8173	Intermediate Similarity	NPC471413
0.8155	Intermediate Similarity	NPC170131
0.8155	Intermediate Similarity	NPC254496
0.8155	Intermediate Similarity	NPC474343
0.8148	Intermediate Similarity	NPC476479
0.8144	Intermediate Similarity	NPC70685
0.8137	Intermediate Similarity	NPC316215
0.8131	Intermediate Similarity	NPC284365
0.8131	Intermediate Similarity	NPC123726
0.8119	Intermediate Similarity	NPC139692
0.8119	Intermediate Similarity	NPC476416
0.8119	Intermediate Similarity	NPC477435
0.8119	Intermediate Similarity	NPC477436
0.8113	Intermediate Similarity	NPC120321
0.8108	Intermediate Similarity	NPC469463
0.8108	Intermediate Similarity	NPC469454
0.8108	Intermediate Similarity	NPC469496
0.81	Intermediate Similarity	NPC134321
0.8095	Intermediate Similarity	NPC81530
0.8095	Intermediate Similarity	NPC476240
0.8095	Intermediate Similarity	NPC207885
0.8095	Intermediate Similarity	NPC224720
0.8095	Intermediate Similarity	NPC471412
0.8095	Intermediate Similarity	NPC112613
0.8095	Intermediate Similarity	NPC476223
0.8091	Intermediate Similarity	NPC317107
0.8081	Intermediate Similarity	NPC473229
0.8077	Intermediate Similarity	NPC23364
0.8058	Intermediate Similarity	NPC234993
0.8058	Intermediate Similarity	NPC134072
0.8058	Intermediate Similarity	NPC202833
0.8053	Intermediate Similarity	NPC472934
0.8053	Intermediate Similarity	NPC469684
0.8053	Intermediate Similarity	NPC243065
0.8039	Intermediate Similarity	NPC477439
0.8039	Intermediate Similarity	NPC269729
0.8037	Intermediate Similarity	NPC258532
0.8037	Intermediate Similarity	NPC296950
0.8036	Intermediate Similarity	NPC238667
0.802	Intermediate Similarity	NPC252433
0.802	Intermediate Similarity	NPC177037
0.802	Intermediate Similarity	NPC233345
0.802	Intermediate Similarity	NPC472814
0.802	Intermediate Similarity	NPC186363
0.8019	Intermediate Similarity	NPC476081
0.8019	Intermediate Similarity	NPC136289
0.8019	Intermediate Similarity	NPC40918
0.8018	Intermediate Similarity	NPC4573
0.8018	Intermediate Similarity	NPC264634
0.8018	Intermediate Similarity	NPC69291
0.8018	Intermediate Similarity	NPC147180
0.8018	Intermediate Similarity	NPC317687
0.8	Intermediate Similarity	NPC472983
0.7982	Intermediate Similarity	NPC275539
0.7982	Intermediate Similarity	NPC189075
0.7982	Intermediate Similarity	NPC306265
0.7982	Intermediate Similarity	NPC251310
0.7981	Intermediate Similarity	NPC285513
0.7981	Intermediate Similarity	NPC38530
0.7981	Intermediate Similarity	NPC84335
0.7981	Intermediate Similarity	NPC287668
0.798	Intermediate Similarity	NPC231599
0.7965	Intermediate Similarity	NPC270478
0.7965	Intermediate Similarity	NPC64318
0.7963	Intermediate Similarity	NPC85529
0.7963	Intermediate Similarity	NPC32006
0.7963	Intermediate Similarity	NPC469607
0.7961	Intermediate Similarity	NPC134067
0.7961	Intermediate Similarity	NPC477437
0.7961	Intermediate Similarity	NPC477438
0.7961	Intermediate Similarity	NPC274417
0.7949	Intermediate Similarity	NPC67251
0.7946	Intermediate Similarity	NPC471204
0.7946	Intermediate Similarity	NPC25909
0.7946	Intermediate Similarity	NPC122056
0.7946	Intermediate Similarity	NPC472929
0.7944	Intermediate Similarity	NPC72151
0.7944	Intermediate Similarity	NPC90177
0.7944	Intermediate Similarity	NPC475526
0.7944	Intermediate Similarity	NPC282233
0.7944	Intermediate Similarity	NPC478057
0.7944	Intermediate Similarity	NPC131366
0.7944	Intermediate Similarity	NPC95585
0.7944	Intermediate Similarity	NPC329345
0.7944	Intermediate Similarity	NPC476889
0.7944	Intermediate Similarity	NPC473283
0.7944	Intermediate Similarity	NPC159533
0.7941	Intermediate Similarity	NPC151722
0.7941	Intermediate Similarity	NPC271652
0.7925	Intermediate Similarity	NPC111292
0.7925	Intermediate Similarity	NPC93744
0.7925	Intermediate Similarity	NPC303559
0.7925	Intermediate Similarity	NPC476888
0.7925	Intermediate Similarity	NPC115862
0.7925	Intermediate Similarity	NPC472637
0.7921	Intermediate Similarity	NPC128672
0.7921	Intermediate Similarity	NPC152467
0.7913	Intermediate Similarity	NPC472933
0.7909	Intermediate Similarity	NPC220705
0.7905	Intermediate Similarity	NPC222011
0.7905	Intermediate Similarity	NPC216478
0.7905	Intermediate Similarity	NPC264378
0.7905	Intermediate Similarity	NPC159763
0.7905	Intermediate Similarity	NPC278386
0.7905	Intermediate Similarity	NPC478056
0.7905	Intermediate Similarity	NPC124512
0.79	Intermediate Similarity	NPC48107
0.79	Intermediate Similarity	NPC104560
0.7895	Intermediate Similarity	NPC474518
0.7895	Intermediate Similarity	NPC134430
0.7895	Intermediate Similarity	NPC23046
0.7895	Intermediate Similarity	NPC239273
0.789	Intermediate Similarity	NPC179380
0.789	Intermediate Similarity	NPC67321
0.789	Intermediate Similarity	NPC284732
0.789	Intermediate Similarity	NPC187435
0.789	Intermediate Similarity	NPC110496
0.789	Intermediate Similarity	NPC44063
0.789	Intermediate Similarity	NPC78966
0.789	Intermediate Similarity	NPC475294
0.789	Intermediate Similarity	NPC472925
0.7885	Intermediate Similarity	NPC29952
0.7885	Intermediate Similarity	NPC184065
0.7881	Intermediate Similarity	NPC470922
0.7881	Intermediate Similarity	NPC24651
0.7881	Intermediate Similarity	NPC476729
0.7879	Intermediate Similarity	NPC473226
0.7876	Intermediate Similarity	NPC67259
0.7876	Intermediate Similarity	NPC147912
0.7864	Intermediate Similarity	NPC272635
0.7864	Intermediate Similarity	NPC477130
0.7864	Intermediate Similarity	NPC477129
0.7864	Intermediate Similarity	NPC169751
0.7864	Intermediate Similarity	NPC471040
0.7863	Intermediate Similarity	NPC312833
0.7857	Intermediate Similarity	NPC470812
0.7857	Intermediate Similarity	NPC100267
0.7857	Intermediate Similarity	NPC475524
0.7857	Intermediate Similarity	NPC285956
0.785	Intermediate Similarity	NPC119601
0.785	Intermediate Similarity	NPC476890
0.785	Intermediate Similarity	NPC320447
0.785	Intermediate Similarity	NPC308726
0.785	Intermediate Similarity	NPC295791
0.785	Intermediate Similarity	NPC164551
0.7845	Intermediate Similarity	NPC476962
0.7843	Intermediate Similarity	NPC72845
0.7843	Intermediate Similarity	NPC99380
0.7843	Intermediate Similarity	NPC472975
0.7843	Intermediate Similarity	NPC472978
0.7838	Intermediate Similarity	NPC235014
0.7838	Intermediate Similarity	NPC472666
0.7835	Intermediate Similarity	NPC470813
0.783	Intermediate Similarity	NPC198880
0.783	Intermediate Similarity	NPC47024
0.783	Intermediate Similarity	NPC474718
0.783	Intermediate Similarity	NPC46761
0.783	Intermediate Similarity	NPC306856
0.783	Intermediate Similarity	NPC35751
0.783	Intermediate Similarity	NPC472972
0.7826	Intermediate Similarity	NPC709
0.7826	Intermediate Similarity	NPC257457
0.7826	Intermediate Similarity	NPC311554

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 NPC1679 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1683
0.2-0.3	3617
0.3-0.4	2280
0.4-0.5	908
0.5-0.6	259
0.6-0.7	162
0.7-0.8	46
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
0.7928	Intermediate Similarity	NPD6650	Approved
0.7928	Intermediate Similarity	NPD6649	Approved
0.7909	Intermediate Similarity	NPD6372	Approved
0.7909	Intermediate Similarity	NPD6373	Approved
0.7905	Intermediate Similarity	NPD4225	Approved
0.789	Intermediate Similarity	NPD5697	Approved
0.7818	Intermediate Similarity	NPD6899	Approved
0.7818	Intermediate Similarity	NPD6881	Approved
0.7798	Intermediate Similarity	NPD7128	Approved
0.7798	Intermediate Similarity	NPD5739	Approved
0.7798	Intermediate Similarity	NPD6675	Approved
0.7798	Intermediate Similarity	NPD6402	Approved
0.7748	Intermediate Similarity	NPD6014	Approved
0.7748	Intermediate Similarity	NPD6012	Approved
0.7748	Intermediate Similarity	NPD6013	Approved
0.7739	Intermediate Similarity	NPD7115	Discovery
0.7727	Intermediate Similarity	NPD5701	Approved
0.7714	Intermediate Similarity	NPD4697	Phase 3
0.7685	Intermediate Similarity	NPD5211	Phase 2
0.7679	Intermediate Similarity	NPD7102	Approved
0.7679	Intermediate Similarity	NPD6883	Approved
0.7679	Intermediate Similarity	NPD7290	Approved
0.7658	Intermediate Similarity	NPD6011	Approved
0.7658	Intermediate Similarity	NPD7320	Approved
0.7642	Intermediate Similarity	NPD7902	Approved
0.7611	Intermediate Similarity	NPD6869	Approved
0.7611	Intermediate Similarity	NPD6847	Approved
0.7611	Intermediate Similarity	NPD6617	Approved
0.7611	Intermediate Similarity	NPD8130	Phase 1
0.7545	Intermediate Similarity	NPD5141	Approved
0.7544	Intermediate Similarity	NPD8297	Approved
0.7544	Intermediate Similarity	NPD6882	Approved
0.75	Intermediate Similarity	NPD5285	Approved
0.75	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD5286	Approved
0.7477	Intermediate Similarity	NPD4755	Approved
0.7426	Intermediate Similarity	NPD1694	Approved
0.7395	Intermediate Similarity	NPD6319	Approved
0.7368	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD4633	Approved
0.7364	Intermediate Similarity	NPD5225	Approved
0.7364	Intermediate Similarity	NPD5224	Approved
0.7364	Intermediate Similarity	NPD5226	Approved
0.7358	Intermediate Similarity	NPD7900	Approved
0.7358	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD7748	Approved
0.735	Intermediate Similarity	NPD6274	Approved
0.7345	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD7640	Approved
0.7339	Intermediate Similarity	NPD7639	Approved
0.7339	Intermediate Similarity	NPD4700	Approved
0.7304	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5174	Approved
0.7297	Intermediate Similarity	NPD5175	Approved
0.729	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5695	Phase 3
0.7282	Intermediate Similarity	NPD3573	Approved
0.7273	Intermediate Similarity	NPD5223	Approved
0.7264	Intermediate Similarity	NPD5779	Approved
0.7264	Intermediate Similarity	NPD6399	Phase 3
0.7264	Intermediate Similarity	NPD5778	Approved
0.7248	Intermediate Similarity	NPD7638	Approved
0.7248	Intermediate Similarity	NPD5696	Approved
0.7222	Intermediate Similarity	NPD5221	Approved
0.7222	Intermediate Similarity	NPD5222	Approved
0.7222	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD4634	Approved
0.72	Intermediate Similarity	NPD7319	Approved
0.7179	Intermediate Similarity	NPD4632	Approved
0.717	Intermediate Similarity	NPD6411	Approved
0.717	Intermediate Similarity	NPD7515	Phase 2
0.7167	Intermediate Similarity	NPD7100	Approved
0.7167	Intermediate Similarity	NPD7101	Approved
0.7156	Intermediate Similarity	NPD5173	Approved
0.7156	Intermediate Similarity	NPD6084	Phase 2
0.7156	Intermediate Similarity	NPD6083	Phase 2
0.7154	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD6317	Approved
0.713	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6054	Approved
0.7105	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6616	Approved
0.7097	Intermediate Similarity	NPD7507	Approved
0.7083	Intermediate Similarity	NPD6313	Approved
0.7083	Intermediate Similarity	NPD6314	Approved
0.7083	Intermediate Similarity	NPD6335	Approved
0.7073	Intermediate Similarity	NPD8328	Phase 3
0.7049	Intermediate Similarity	NPD6015	Approved
0.7049	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD6016	Approved
0.7043	Intermediate Similarity	NPD4730	Approved
0.7043	Intermediate Similarity	NPD4729	Approved
0.7043	Intermediate Similarity	NPD5128	Approved
0.704	Intermediate Similarity	NPD7078	Approved
0.7019	Intermediate Similarity	NPD3618	Phase 1
0.7019	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6008	Approved
0.7018	Intermediate Similarity	NPD4768	Approved
0.7018	Intermediate Similarity	NPD4767	Approved
0.7009	Intermediate Similarity	NPD5693	Phase 1
0.7009	Intermediate Similarity	NPD6079	Approved
0.7	Intermediate Similarity	NPD6009	Approved
0.6992	Remote Similarity	NPD6370	Approved
0.6992	Remote Similarity	NPD5988	Approved
0.6991	Remote Similarity	NPD4754	Approved
0.6984	Remote Similarity	NPD7736	Approved
0.6981	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5328	Approved
0.6981	Remote Similarity	NPD6101	Approved
0.6967	Remote Similarity	NPD6059	Approved
0.6923	Remote Similarity	NPD5247	Approved
0.6923	Remote Similarity	NPD5250	Approved
0.6923	Remote Similarity	NPD5251	Approved
0.6923	Remote Similarity	NPD5249	Phase 3
0.6923	Remote Similarity	NPD5248	Approved
0.6917	Remote Similarity	NPD6868	Approved
0.6916	Remote Similarity	NPD5785	Approved
0.6911	Remote Similarity	NPD6909	Approved
0.6911	Remote Similarity	NPD6908	Approved
0.6911	Remote Similarity	NPD5983	Phase 2
0.6905	Remote Similarity	NPD8293	Discontinued
0.6897	Remote Similarity	NPD6686	Approved
0.6887	Remote Similarity	NPD6672	Approved
0.6887	Remote Similarity	NPD5737	Approved
0.6864	Remote Similarity	NPD5216	Approved
0.6864	Remote Similarity	NPD5215	Approved
0.6864	Remote Similarity	NPD5217	Approved
0.6852	Remote Similarity	NPD8035	Phase 2
0.6852	Remote Similarity	NPD8034	Phase 2
0.6822	Remote Similarity	NPD4753	Phase 2
0.6818	Remote Similarity	NPD4629	Approved
0.6818	Remote Similarity	NPD5210	Approved
0.681	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6053	Discontinued
0.68	Remote Similarity	NPD7604	Phase 2
0.6789	Remote Similarity	NPD4202	Approved
0.678	Remote Similarity	NPD5135	Approved
0.678	Remote Similarity	NPD6371	Approved
0.678	Remote Similarity	NPD5169	Approved
0.678	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD4695	Discontinued
0.6754	Remote Similarity	NPD7632	Discontinued
0.6727	Remote Similarity	NPD5282	Discontinued
0.6723	Remote Similarity	NPD5127	Approved
0.6721	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6409	Approved
0.6698	Remote Similarity	NPD7334	Approved
0.6698	Remote Similarity	NPD7146	Approved
0.6698	Remote Similarity	NPD5330	Approved
0.6698	Remote Similarity	NPD7521	Approved
0.6698	Remote Similarity	NPD6684	Approved
0.6697	Remote Similarity	NPD5281	Approved
0.6697	Remote Similarity	NPD5284	Approved
0.6693	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.664	Remote Similarity	NPD8517	Approved
0.664	Remote Similarity	NPD8513	Phase 3
0.664	Remote Similarity	NPD8516	Approved
0.664	Remote Similarity	NPD8515	Approved
0.664	Remote Similarity	NPD6921	Approved
0.661	Remote Similarity	NPD5168	Approved
0.6606	Remote Similarity	NPD5692	Phase 3
0.6604	Remote Similarity	NPD1696	Phase 3
0.6579	Remote Similarity	NPD6648	Approved
0.6574	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6903	Approved
0.6565	Remote Similarity	NPD7260	Phase 2
0.6557	Remote Similarity	NPD5167	Approved
0.6545	Remote Similarity	NPD5694	Approved
0.6545	Remote Similarity	NPD6050	Approved
0.6542	Remote Similarity	NPD4519	Discontinued
0.6542	Remote Similarity	NPD5690	Phase 2
0.6542	Remote Similarity	NPD5786	Approved
0.6542	Remote Similarity	NPD5279	Phase 3
0.6542	Remote Similarity	NPD4623	Approved
0.6514	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD3665	Phase 1
0.6509	Remote Similarity	NPD3666	Approved
0.6509	Remote Similarity	NPD4197	Approved
0.6509	Remote Similarity	NPD3133	Approved
0.6476	Remote Similarity	NPD3667	Approved
0.6462	Remote Similarity	NPD6033	Approved
0.6455	Remote Similarity	NPD6698	Approved
0.6455	Remote Similarity	NPD46	Approved
0.6449	Remote Similarity	NPD5329	Approved
0.6449	Remote Similarity	NPD5363	Approved
0.6429	Remote Similarity	NPD6001	Approved
0.6417	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6396	Remote Similarity	NPD7637	Suspended
0.6396	Remote Similarity	NPD7983	Approved
0.6389	Remote Similarity	NPD4694	Approved
0.6389	Remote Similarity	NPD6098	Approved
0.6389	Remote Similarity	NPD5280	Approved
0.6385	Remote Similarity	NPD8074	Phase 3
0.6364	Remote Similarity	NPD6051	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