NPASS Compound

Structure

NPC469802 OpenBabel07101718242D 32 33 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 2.5981 -6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 -1.3660 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 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 2.5981 -4.5000 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 0.8660 1.5000 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 1.7321 -2.0000 0.0000 C 0 0 2 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 0 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 0.8660 -6.5000 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 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 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 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 2 0 0 0 0 3 18 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 25 1 0 0 0 0 7 25 1 0 0 0 0 9 11 1 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 10 16 2 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 30 1 0 0 0 0 14 21 1 0 0 0 0 15 23 1 0 0 0 0 15 24 1 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 27 2 0 0 0 0 18 30 1 0 0 0 0 19 28 2 0 0 0 0 19 31 1 0 0 0 0 20 29 2 0 0 0 0 20 32 1 0 0 0 0 21 26 1 6 0 0 0 22 14 1 1 0 0 0 22 31 1 0 0 0 0 23 32 1 1 0 0 0 24 25 1 0 0 0 0 24 26 1 6 0 0 0 26 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.28
Volume:	480.698
LogP:	4.033
LogD:	3.304
LogS:	-4.547
# Rotatable Bonds:	10
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.304
Synthetic Accessibility Score:	4.604
Fsp3:	0.731
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:	-4.69
MDCK Permeability:	4.718591662822291e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.02
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	0.726
30% Bioavailability (F30%):	0.925

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.109
Plasma Protein Binding (PPB):	83.4506607055664%
Volume Distribution (VD):	1.674
Pgp-substrate:	17.901872634887695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.056
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.281
CYP2C9-inhibitor:	0.377
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.051
CYP2D6-substrate:	0.129
CYP3A4-inhibitor:	0.502
CYP3A4-substrate:	0.337

ADMET: Excretion

Clearance (CL):	3.591
Half-life (T1/2):	0.176

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.827
Drug-inuced Liver Injury (DILI):	0.828
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.142
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.211
Carcinogencity:	0.059
Eye Corrosion:	0.136
Eye Irritation:	0.373
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC469802

Natural Product ID:	NPC469802
*Common Name:**	(R)-5-((1R,3R,4As,8Ar)-3-Acetoxy-4A,5,5,8A-Tetramethyl-2-Methylenedecahydronaphthalen-1-Yl)-3-Methylpent-2-Ene-1,4-Diyl Diacetate
IUPAC Name:	[(E,4R)-5-[(1R,3R,4aS,8aS)-3-acetyloxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-4-acetyloxy-3-methylpent-2-enyl] acetate
Synonyms:
Standard InCHIKey:	SJLYWQVJQJFQKI-RCAHKWKJSA-N
Standard InCHI:	InChI=1S/C26H40O6/c1-16(10-13-30-18(3)27)22(31-19(4)28)14-21-17(2)23(32-20(5)29)15-24-25(6,7)11-9-12-26(21,24)8/h10,21-24H,2,9,11-15H2,1,3-8H3/b16-10+/t21-,22+,23+,24-,26+/m0/s1
SMILES:	CC(=O)OC/C=C(/[C@@H](C[C@H]1C(=C)[C@H](OC(=O)C)C[C@@H]2[C@]1(C)CCCC2(C)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1173547
PubChem CID:	49799348
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
NPO23525	Physalis sordida	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20575572]
NPO23525	Physalis sordida	Species	Solanaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	29.4	%	PMID[504295]

☑ 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 NPC469802 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	201
0.1-0.2	1371
0.2-0.3	4671
0.3-0.4	12289
0.4-0.5	11011
0.5-0.6	6870
0.6-0.7	5137
0.7-0.8	1071
0.8-0.85	61
0.85-0.9	13
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC102048
0.8795	High Similarity	NPC106332
0.878	High Similarity	NPC102996
0.869	High Similarity	NPC246028
0.8675	High Similarity	NPC102640
0.8659	High Similarity	NPC474013
0.8625	High Similarity	NPC170303
0.8625	High Similarity	NPC25554
0.8605	High Similarity	NPC7349
0.8571	High Similarity	NPC69713
0.8537	High Similarity	NPC96055
0.8519	High Similarity	NPC471218
0.8506	High Similarity	NPC105490
0.8506	High Similarity	NPC140277
0.8488	Intermediate Similarity	NPC234335
0.8471	Intermediate Similarity	NPC261320
0.8452	Intermediate Similarity	NPC166857
0.8375	Intermediate Similarity	NPC242767
0.8372	Intermediate Similarity	NPC232202
0.8372	Intermediate Similarity	NPC220216
0.8354	Intermediate Similarity	NPC189206
0.8353	Intermediate Similarity	NPC93411
0.8353	Intermediate Similarity	NPC473879
0.8353	Intermediate Similarity	NPC291665
0.8333	Intermediate Similarity	NPC131813
0.8315	Intermediate Similarity	NPC475380
0.8315	Intermediate Similarity	NPC94905
0.8315	Intermediate Similarity	NPC209297
0.8315	Intermediate Similarity	NPC194132
0.8315	Intermediate Similarity	NPC8954
0.8293	Intermediate Similarity	NPC256112
0.8276	Intermediate Similarity	NPC473944
0.8276	Intermediate Similarity	NPC477574
0.8276	Intermediate Similarity	NPC124374
0.8272	Intermediate Similarity	NPC233332
0.8256	Intermediate Similarity	NPC170633
0.8235	Intermediate Similarity	NPC471779
0.8222	Intermediate Similarity	NPC100912
0.8222	Intermediate Similarity	NPC475446
0.8222	Intermediate Similarity	NPC51499
0.8222	Intermediate Similarity	NPC311241
0.8214	Intermediate Similarity	NPC35933
0.8202	Intermediate Similarity	NPC471362
0.8202	Intermediate Similarity	NPC471372
0.8202	Intermediate Similarity	NPC472189
0.8202	Intermediate Similarity	NPC276110
0.8193	Intermediate Similarity	NPC476927
0.8182	Intermediate Similarity	NPC99653
0.8171	Intermediate Similarity	NPC14203
0.8171	Intermediate Similarity	NPC229584
0.8161	Intermediate Similarity	NPC78973
0.8132	Intermediate Similarity	NPC107806
0.8132	Intermediate Similarity	NPC325229
0.8132	Intermediate Similarity	NPC72647
0.8132	Intermediate Similarity	NPC275086
0.8118	Intermediate Similarity	NPC329692
0.8118	Intermediate Similarity	NPC286153
0.8118	Intermediate Similarity	NPC471219
0.8111	Intermediate Similarity	NPC171598
0.8095	Intermediate Similarity	NPC32223
0.8095	Intermediate Similarity	NPC306951
0.809	Intermediate Similarity	NPC472416
0.809	Intermediate Similarity	NPC161998
0.809	Intermediate Similarity	NPC57117
0.809	Intermediate Similarity	NPC472360
0.809	Intermediate Similarity	NPC477722
0.8072	Intermediate Similarity	NPC286786
0.8068	Intermediate Similarity	NPC41239
0.8068	Intermediate Similarity	NPC329842
0.8049	Intermediate Similarity	NPC281880
0.8049	Intermediate Similarity	NPC269791
0.8046	Intermediate Similarity	NPC16265
0.8043	Intermediate Similarity	NPC219285
0.8043	Intermediate Similarity	NPC228251
0.8043	Intermediate Similarity	NPC161527
0.8043	Intermediate Similarity	NPC251680
0.8043	Intermediate Similarity	NPC477971
0.8043	Intermediate Similarity	NPC477968
0.8043	Intermediate Similarity	NPC477972
0.8043	Intermediate Similarity	NPC20113
0.8043	Intermediate Similarity	NPC471413
0.8043	Intermediate Similarity	NPC324841
0.8023	Intermediate Similarity	NPC264546
0.8022	Intermediate Similarity	NPC472188
0.8	Intermediate Similarity	NPC471786
0.8	Intermediate Similarity	NPC281134
0.8	Intermediate Similarity	NPC37603
0.7978	Intermediate Similarity	NPC53555
0.7976	Intermediate Similarity	NPC12283
0.7976	Intermediate Similarity	NPC49208
0.7976	Intermediate Similarity	NPC311070
0.7976	Intermediate Similarity	NPC132386
0.7976	Intermediate Similarity	NPC222358
0.7976	Intermediate Similarity	NPC474193
0.7976	Intermediate Similarity	NPC23748
0.7975	Intermediate Similarity	NPC306727
0.7973	Intermediate Similarity	NPC329698
0.7957	Intermediate Similarity	NPC475617
0.7957	Intermediate Similarity	NPC268829
0.7957	Intermediate Similarity	NPC471412
0.7957	Intermediate Similarity	NPC25177
0.7957	Intermediate Similarity	NPC11974
0.7957	Intermediate Similarity	NPC222875
0.7957	Intermediate Similarity	NPC247701
0.7957	Intermediate Similarity	NPC295110
0.7955	Intermediate Similarity	NPC48732
0.7952	Intermediate Similarity	NPC159148
0.7952	Intermediate Similarity	NPC142163
0.7952	Intermediate Similarity	NPC195334
0.7952	Intermediate Similarity	NPC290495
0.7949	Intermediate Similarity	NPC477084
0.7935	Intermediate Similarity	NPC476800
0.7935	Intermediate Similarity	NPC318917
0.7935	Intermediate Similarity	NPC472186
0.7935	Intermediate Similarity	NPC278673
0.7935	Intermediate Similarity	NPC471366
0.7931	Intermediate Similarity	NPC470613
0.7931	Intermediate Similarity	NPC470612
0.7927	Intermediate Similarity	NPC44083
0.7927	Intermediate Similarity	NPC153987
0.7927	Intermediate Similarity	NPC100906
0.7922	Intermediate Similarity	NPC269841
0.7912	Intermediate Similarity	NPC284194
0.7912	Intermediate Similarity	NPC276103
0.7912	Intermediate Similarity	NPC134072
0.7912	Intermediate Similarity	NPC471765
0.7912	Intermediate Similarity	NPC54248
0.7912	Intermediate Similarity	NPC234993
0.7912	Intermediate Similarity	NPC211810
0.7912	Intermediate Similarity	NPC221801
0.7901	Intermediate Similarity	NPC470750
0.7901	Intermediate Similarity	NPC470751
0.7889	Intermediate Similarity	NPC474922
0.7889	Intermediate Similarity	NPC88507
0.7882	Intermediate Similarity	NPC471367
0.7882	Intermediate Similarity	NPC318515
0.7872	Intermediate Similarity	NPC162973
0.7872	Intermediate Similarity	NPC475038
0.7872	Intermediate Similarity	NPC109195
0.7872	Intermediate Similarity	NPC475344
0.7872	Intermediate Similarity	NPC476471
0.7865	Intermediate Similarity	NPC472811
0.7865	Intermediate Similarity	NPC72845
0.7865	Intermediate Similarity	NPC476417
0.7865	Intermediate Similarity	NPC177641
0.7857	Intermediate Similarity	NPC200513
0.7857	Intermediate Similarity	NPC2524
0.7849	Intermediate Similarity	NPC473545
0.7849	Intermediate Similarity	NPC38855
0.7849	Intermediate Similarity	NPC16601
0.7849	Intermediate Similarity	NPC472187
0.7849	Intermediate Similarity	NPC473204
0.7841	Intermediate Similarity	NPC82876
0.7841	Intermediate Similarity	NPC177141
0.7841	Intermediate Similarity	NPC50488
0.7841	Intermediate Similarity	NPC293044
0.7841	Intermediate Similarity	NPC474396
0.7831	Intermediate Similarity	NPC268827
0.7826	Intermediate Similarity	NPC473244
0.7816	Intermediate Similarity	NPC131329
0.7816	Intermediate Similarity	NPC175293
0.7816	Intermediate Similarity	NPC471796
0.7805	Intermediate Similarity	NPC184737
0.7791	Intermediate Similarity	NPC30984
0.7791	Intermediate Similarity	NPC472442
0.7791	Intermediate Similarity	NPC164424
0.7789	Intermediate Similarity	NPC473523
0.7789	Intermediate Similarity	NPC97487
0.7789	Intermediate Similarity	NPC10232
0.7789	Intermediate Similarity	NPC281378
0.7789	Intermediate Similarity	NPC160583
0.7789	Intermediate Similarity	NPC189588
0.7789	Intermediate Similarity	NPC187302
0.7789	Intermediate Similarity	NPC254202
0.7789	Intermediate Similarity	NPC196471
0.7789	Intermediate Similarity	NPC474124
0.7789	Intermediate Similarity	NPC120009
0.7789	Intermediate Similarity	NPC45897
0.7778	Intermediate Similarity	NPC472812
0.7778	Intermediate Similarity	NPC162615
0.7778	Intermediate Similarity	NPC475657
0.7778	Intermediate Similarity	NPC472640
0.7778	Intermediate Similarity	NPC139692
0.7778	Intermediate Similarity	NPC152778
0.7778	Intermediate Similarity	NPC205034
0.7778	Intermediate Similarity	NPC472641
0.7778	Intermediate Similarity	NPC473678
0.7766	Intermediate Similarity	NPC472554
0.7765	Intermediate Similarity	NPC79945
0.7765	Intermediate Similarity	NPC472440
0.7765	Intermediate Similarity	NPC473742
0.7765	Intermediate Similarity	NPC139206
0.7765	Intermediate Similarity	NPC477124
0.7763	Intermediate Similarity	NPC185587
0.7753	Intermediate Similarity	NPC310479
0.7753	Intermediate Similarity	NPC182136
0.7753	Intermediate Similarity	NPC221111
0.7753	Intermediate Similarity	NPC280149
0.7753	Intermediate Similarity	NPC209816
0.7753	Intermediate Similarity	NPC302280

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 NPC469802 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1583
0.2-0.3	3941
0.3-0.4	2272
0.4-0.5	747
0.5-0.6	277
0.6-0.7	142
0.7-0.8	7
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
0.8132	Intermediate Similarity	NPD7638	Approved
0.8043	Intermediate Similarity	NPD7640	Approved
0.8043	Intermediate Similarity	NPD7639	Approved
0.7857	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD6051	Approved
0.7368	Intermediate Similarity	NPD4225	Approved
0.732	Intermediate Similarity	NPD7632	Discontinued
0.7129	Intermediate Similarity	NPD6686	Approved
0.7128	Intermediate Similarity	NPD7900	Approved
0.7128	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7748	Approved
0.7113	Intermediate Similarity	NPD6648	Approved
0.7111	Intermediate Similarity	NPD7146	Approved
0.7111	Intermediate Similarity	NPD6684	Approved
0.7111	Intermediate Similarity	NPD5330	Approved
0.7111	Intermediate Similarity	NPD6409	Approved
0.7111	Intermediate Similarity	NPD7521	Approved
0.7111	Intermediate Similarity	NPD7334	Approved
0.7097	Intermediate Similarity	NPD7637	Suspended
0.7051	Intermediate Similarity	NPD5325	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5344	Discontinued
0.7024	Intermediate Similarity	NPD8039	Approved
0.7021	Intermediate Similarity	NPD6399	Phase 3
0.7	Intermediate Similarity	NPD1694	Approved
0.6966	Remote Similarity	NPD6695	Phase 3
0.6962	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5737	Approved
0.6957	Remote Similarity	NPD6903	Approved
0.6957	Remote Similarity	NPD6672	Approved
0.6957	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7515	Phase 2
0.6907	Remote Similarity	NPD7902	Approved
0.6897	Remote Similarity	NPD7645	Phase 2
0.6889	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7328	Approved
0.6852	Remote Similarity	NPD7327	Approved
0.6842	Remote Similarity	NPD5779	Approved
0.6842	Remote Similarity	NPD5778	Approved
0.6818	Remote Similarity	NPD7525	Registered
0.6789	Remote Similarity	NPD7516	Approved
0.6765	Remote Similarity	NPD6008	Approved
0.6737	Remote Similarity	NPD5693	Phase 1
0.6731	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD8377	Approved
0.6727	Remote Similarity	NPD8294	Approved
0.6705	Remote Similarity	NPD6929	Approved
0.6703	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD7750	Discontinued
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD7524	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6632	Remote Similarity	NPD6698	Approved
0.6632	Remote Similarity	NPD7838	Discovery
0.6632	Remote Similarity	NPD46	Approved
0.6629	Remote Similarity	NPD6931	Approved
0.6629	Remote Similarity	NPD6930	Phase 2
0.6628	Remote Similarity	NPD6942	Approved
0.6628	Remote Similarity	NPD7339	Approved
0.6628	Remote Similarity	NPD8264	Approved
0.6562	Remote Similarity	NPD8034	Phase 2
0.6562	Remote Similarity	NPD8035	Phase 2
0.6562	Remote Similarity	NPD6411	Approved
0.6559	Remote Similarity	NPD6098	Approved
0.6552	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD6673	Approved
0.6526	Remote Similarity	NPD6080	Approved
0.6526	Remote Similarity	NPD6904	Approved
0.6522	Remote Similarity	NPD3668	Phase 3
0.6522	Remote Similarity	NPD4786	Approved
0.6518	Remote Similarity	NPD7503	Approved
0.6512	Remote Similarity	NPD6926	Approved
0.6512	Remote Similarity	NPD6924	Approved
0.6489	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5209	Approved
0.6484	Remote Similarity	NPD3667	Approved
0.6477	Remote Similarity	NPD5776	Phase 2
0.6477	Remote Similarity	NPD6925	Approved
0.6476	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7115	Discovery
0.6452	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7514	Phase 3
0.6444	Remote Similarity	NPD7332	Phase 2
0.6442	Remote Similarity	NPD7128	Approved
0.6442	Remote Similarity	NPD6675	Approved
0.6442	Remote Similarity	NPD5739	Approved
0.6442	Remote Similarity	NPD6402	Approved
0.6435	Remote Similarity	NPD7507	Approved
0.6404	Remote Similarity	NPD7145	Approved
0.64	Remote Similarity	NPD6083	Phase 2
0.64	Remote Similarity	NPD6084	Phase 2
0.6392	Remote Similarity	NPD7087	Discontinued
0.6383	Remote Similarity	NPD3618	Phase 1
0.6374	Remote Similarity	NPD6902	Approved
0.6364	Remote Similarity	NPD6933	Approved
0.6354	Remote Similarity	NPD5328	Approved
0.6354	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6101	Approved
0.6337	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.633	Remote Similarity	NPD8133	Approved
0.6321	Remote Similarity	NPD6881	Approved
0.6321	Remote Similarity	NPD7320	Approved
0.6321	Remote Similarity	NPD6899	Approved
0.6292	Remote Similarity	NPD6932	Approved
0.6279	Remote Similarity	NPD7151	Approved
0.6279	Remote Similarity	NPD7150	Approved
0.6279	Remote Similarity	NPD7152	Approved
0.6277	Remote Similarity	NPD6893	Approved
0.6271	Remote Similarity	NPD7319	Approved
0.6264	Remote Similarity	NPD7509	Discontinued
0.6262	Remote Similarity	NPD6372	Approved
0.6262	Remote Similarity	NPD6373	Approved
0.6262	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5208	Approved
0.6239	Remote Similarity	NPD6053	Discontinued
0.6235	Remote Similarity	NPD6923	Approved
0.6235	Remote Similarity	NPD6922	Approved
0.6226	Remote Similarity	NPD6412	Phase 2
0.6226	Remote Similarity	NPD5697	Approved
0.6226	Remote Similarity	NPD5701	Approved
0.6224	Remote Similarity	NPD6050	Approved
0.6224	Remote Similarity	NPD6079	Approved
0.6222	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6883	Approved
0.6204	Remote Similarity	NPD7290	Approved
0.6204	Remote Similarity	NPD7102	Approved
0.62	Remote Similarity	NPD5695	Phase 3
0.6196	Remote Similarity	NPD6898	Phase 1
0.6186	Remote Similarity	NPD1695	Approved
0.6182	Remote Similarity	NPD4632	Approved
0.6176	Remote Similarity	NPD5696	Approved
0.617	Remote Similarity	NPD3665	Phase 1
0.617	Remote Similarity	NPD3133	Approved
0.617	Remote Similarity	NPD3666	Approved
0.6168	Remote Similarity	NPD6011	Approved
0.6163	Remote Similarity	NPD7143	Approved
0.6163	Remote Similarity	NPD7144	Approved
0.6154	Remote Similarity	NPD6683	Phase 2
0.6147	Remote Similarity	NPD8130	Phase 1
0.6147	Remote Similarity	NPD6650	Approved
0.6147	Remote Similarity	NPD6617	Approved
0.6147	Remote Similarity	NPD6649	Approved
0.6147	Remote Similarity	NPD6869	Approved
0.6147	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6847	Approved
0.6146	Remote Similarity	NPD4251	Approved
0.6146	Remote Similarity	NPD4250	Approved
0.6122	Remote Similarity	NPD5785	Approved
0.6122	Remote Similarity	NPD5692	Phase 3
0.6122	Remote Similarity	NPD3168	Discontinued
0.6111	Remote Similarity	NPD6014	Approved
0.6111	Remote Similarity	NPD6013	Approved
0.6111	Remote Similarity	NPD6012	Approved
0.6105	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.61	Remote Similarity	NPD6001	Approved
0.6092	Remote Similarity	NPD4243	Approved
0.6091	Remote Similarity	NPD6882	Approved
0.6091	Remote Similarity	NPD8297	Approved
0.6087	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4695	Discontinued
0.6064	Remote Similarity	NPD5362	Discontinued
0.6064	Remote Similarity	NPD7154	Phase 3
0.6061	Remote Similarity	NPD5694	Approved
0.6061	Remote Similarity	NPD7983	Approved
0.6055	Remote Similarity	NPD6371	Approved
0.6044	Remote Similarity	NPD6114	Approved
0.6044	Remote Similarity	NPD6115	Approved
0.6044	Remote Similarity	NPD6697	Approved
0.6044	Remote Similarity	NPD6118	Approved
0.6042	Remote Similarity	NPD4249	Approved
0.602	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD6009	Approved
0.6	Remote Similarity	NPD4202	Approved
0.6	Remote Similarity	NPD6319	Approved
0.5983	Remote Similarity	NPD7604	Phase 2
0.5983	Remote Similarity	NPD8328	Phase 3
0.5981	Remote Similarity	NPD6640	Phase 3
0.598	Remote Similarity	NPD7732	Phase 3
0.598	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.598	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.598	Remote Similarity	NPD4697	Phase 3
0.598	Remote Similarity	NPD5221	Approved
0.598	Remote Similarity	NPD5222	Approved
0.5978	Remote Similarity	NPD4195	Approved
0.596	Remote Similarity	NPD5207	Approved
0.5955	Remote Similarity	NPD4785	Approved
0.5955	Remote Similarity	NPD4784	Approved
0.5948	Remote Similarity	NPD5983	Phase 2
0.5941	Remote Similarity	NPD5707	Approved
0.5932	Remote Similarity	NPD7492	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