NPASS Compound

Structure

CID82876 OpenBabel06191715422D 23 24 0 0 1 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 6.9282 0.0000 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 4.3301 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 2.0000 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 1.7321 -0.0000 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 0.5000 0.0000 C 0 0 2 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 -0.8660 0.5000 0.0000 C 0 0 2 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 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 6.0622 0.5000 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 1 12 1 0 0 0 0 4 22 1 0 0 0 0 5 6 2 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 15 1 0 0 0 0 9 17 1 0 0 0 0 10 17 1 0 0 0 0 11 13 1 0 0 0 0 11 14 1 0 0 0 0 12 19 2 0 0 0 0 12 23 1 0 0 0 0 13 5 1 1 0 0 0 14 17 1 1 0 0 0 14 18 1 0 0 0 0 15 18 1 6 0 0 0 15 23 1 0 0 0 0 16 20 2 0 0 0 0 16 22 1 0 0 0 0 17 2 1 1 0 0 0 18 3 1 1 0 0 0 18 21 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	324.19
Volume:	338.813
LogP:	2.603
LogD:	2.105
LogS:	-2.52
# Rotatable Bonds:	5
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.638
Synthetic Accessibility Score:	4.334
Fsp3:	0.778
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:	-4.669
MDCK Permeability:	4.353788972366601e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.857
30% Bioavailability (F30%):	0.958

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.764
Plasma Protein Binding (PPB):	71.86318969726562%
Volume Distribution (VD):	1.252
Pgp-substrate:	29.146841049194336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.229
CYP2C19-inhibitor:	0.113
CYP2C19-substrate:	0.734
CYP2C9-inhibitor:	0.07
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.106
CYP3A4-inhibitor:	0.358
CYP3A4-substrate:	0.433

ADMET: Excretion

Clearance (CL):	4.26
Half-life (T1/2):	0.687

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.713
Drug-inuced Liver Injury (DILI):	0.133
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.73
Skin Sensitization:	0.901
Carcinogencity:	0.09
Eye Corrosion:	0.025
Eye Irritation:	0.088
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC82876

Natural Product ID:	NPC82876
*Common Name:**	3Alpha-Acetoxy-4Alpha-Hydroxy-4Beta,10Beta-Dimethyl-7Beta-(Methyl 1E-Propenoate)-Trans-Decalin
IUPAC Name:	methyl (E)-3-[(2R,4aS,7R,8S,8aR)-7-acetyloxy-8-hydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoate
Synonyms:	3alpha-acetoxydiversifolol
Standard InCHIKey:	BWEZAELZEOOOJT-POCSJANHSA-N
Standard InCHI:	InChI=1S/C18H28O5/c1-12(19)23-15-8-10-17(2)9-7-13(5-6-16(20)22-4)11-14(17)18(15,3)21/h5-6,13-15,21H,7-11H2,1-4H3/b6-5+/t13-,14-,15-,17+,18+/m1/s1
SMILES:	CC(=O)O[C@@H]1CC[C@]2(C)CC[C@@H](/C=C/C(=O)OC)C[C@H]2[C@]1(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464699
PubChem CID:	11120895
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

*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
NPO19764	Tithonia diversifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11975495]
NPO19764	Tithonia diversifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO19764	Tithonia diversifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO19764	Tithonia diversifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19764	Tithonia diversifolia	Species	Asteraceae	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
IC50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	<	10.0	ug.mL-1	PMID[485172]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[485172]

☑ 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 NPC82876 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	196
0.1-0.2	1234
0.2-0.3	4203
0.3-0.4	9056
0.4-0.5	13156
0.5-0.6	7497
0.6-0.7	5854
0.7-0.8	1381
0.8-0.85	101
0.85-0.9	18
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8736	High Similarity	NPC175145
0.8736	High Similarity	NPC475069
0.8696	High Similarity	NPC473153
0.8605	High Similarity	NPC49208
0.8605	High Similarity	NPC476927
0.8571	High Similarity	NPC53555
0.8523	High Similarity	NPC131813
0.8462	Intermediate Similarity	NPC303697
0.8444	Intermediate Similarity	NPC20946
0.8438	Intermediate Similarity	NPC283343
0.8438	Intermediate Similarity	NPC258547
0.8438	Intermediate Similarity	NPC11956
0.8427	Intermediate Similarity	NPC473891
0.8427	Intermediate Similarity	NPC131329
0.8421	Intermediate Similarity	NPC38855
0.8404	Intermediate Similarity	NPC210337
0.8391	Intermediate Similarity	NPC23748
0.8391	Intermediate Similarity	NPC79945
0.8372	Intermediate Similarity	NPC170303
0.837	Intermediate Similarity	NPC162615
0.837	Intermediate Similarity	NPC7349
0.837	Intermediate Similarity	NPC205034
0.837	Intermediate Similarity	NPC152778
0.8352	Intermediate Similarity	NPC78973
0.8352	Intermediate Similarity	NPC310479
0.8351	Intermediate Similarity	NPC23584
0.8333	Intermediate Similarity	NPC472554
0.8333	Intermediate Similarity	NPC473160
0.8316	Intermediate Similarity	NPC278386
0.8316	Intermediate Similarity	NPC159763
0.8316	Intermediate Similarity	NPC124512
0.8298	Intermediate Similarity	NPC88009
0.8295	Intermediate Similarity	NPC306951
0.828	Intermediate Similarity	NPC105490
0.828	Intermediate Similarity	NPC201725
0.8276	Intermediate Similarity	NPC256112
0.8276	Intermediate Similarity	NPC2524
0.8261	Intermediate Similarity	NPC329842
0.8261	Intermediate Similarity	NPC72845
0.8247	Intermediate Similarity	NPC472815
0.8247	Intermediate Similarity	NPC273668
0.8247	Intermediate Similarity	NPC472552
0.8229	Intermediate Similarity	NPC474190
0.8229	Intermediate Similarity	NPC473510
0.8229	Intermediate Similarity	NPC230546
0.8222	Intermediate Similarity	NPC166857
0.8222	Intermediate Similarity	NPC245004
0.8211	Intermediate Similarity	NPC231751
0.8211	Intermediate Similarity	NPC73911
0.8202	Intermediate Similarity	NPC474013
0.8202	Intermediate Similarity	NPC35933
0.8191	Intermediate Similarity	NPC472441
0.8191	Intermediate Similarity	NPC276110
0.8182	Intermediate Similarity	NPC88349
0.8172	Intermediate Similarity	NPC139692
0.8163	Intermediate Similarity	NPC281378
0.8161	Intermediate Similarity	NPC25554
0.8152	Intermediate Similarity	NPC182136
0.8152	Intermediate Similarity	NPC302280
0.8144	Intermediate Similarity	NPC11974
0.8132	Intermediate Similarity	NPC93411
0.8132	Intermediate Similarity	NPC106332
0.8125	Intermediate Similarity	NPC316598
0.8105	Intermediate Similarity	NPC16967
0.8085	Intermediate Similarity	NPC191521
0.8085	Intermediate Similarity	NPC57117
0.8085	Intermediate Similarity	NPC469491
0.8065	Intermediate Similarity	NPC472811
0.8046	Intermediate Similarity	NPC281880
0.8046	Intermediate Similarity	NPC233332
0.8043	Intermediate Similarity	NPC246028
0.8043	Intermediate Similarity	NPC50488
0.8043	Intermediate Similarity	NPC170633
0.8043	Intermediate Similarity	NPC474396
0.8041	Intermediate Similarity	NPC471413
0.8022	Intermediate Similarity	NPC473097
0.8022	Intermediate Similarity	NPC476948
0.802	Intermediate Similarity	NPC181994
0.802	Intermediate Similarity	NPC475418
0.802	Intermediate Similarity	NPC475263
0.802	Intermediate Similarity	NPC473482
0.802	Intermediate Similarity	NPC318363
0.8	Intermediate Similarity	NPC51719
0.8	Intermediate Similarity	NPC109528
0.8	Intermediate Similarity	NPC186668
0.8	Intermediate Similarity	NPC477125
0.8	Intermediate Similarity	NPC471206
0.798	Intermediate Similarity	NPC297617
0.798	Intermediate Similarity	NPC474575
0.798	Intermediate Similarity	NPC472821
0.7979	Intermediate Similarity	NPC38232
0.7979	Intermediate Similarity	NPC110022
0.7979	Intermediate Similarity	NPC472812
0.7978	Intermediate Similarity	NPC311070
0.7961	Intermediate Similarity	NPC470076
0.7959	Intermediate Similarity	NPC475617
0.7959	Intermediate Similarity	NPC471412
0.7959	Intermediate Similarity	NPC303559
0.7957	Intermediate Similarity	NPC221111
0.7957	Intermediate Similarity	NPC280149
0.7955	Intermediate Similarity	NPC159148
0.7941	Intermediate Similarity	NPC475065
0.7938	Intermediate Similarity	NPC108368
0.7938	Intermediate Similarity	NPC57079
0.7938	Intermediate Similarity	NPC474440
0.7938	Intermediate Similarity	NPC218107
0.7938	Intermediate Similarity	NPC475068
0.7938	Intermediate Similarity	NPC278673
0.7931	Intermediate Similarity	NPC233295
0.7921	Intermediate Similarity	NPC122816
0.7921	Intermediate Similarity	NPC329048
0.7921	Intermediate Similarity	NPC471205
0.7921	Intermediate Similarity	NPC473586
0.7921	Intermediate Similarity	NPC330011
0.7921	Intermediate Similarity	NPC67321
0.7921	Intermediate Similarity	NPC187435
0.7917	Intermediate Similarity	NPC134072
0.7917	Intermediate Similarity	NPC242848
0.7917	Intermediate Similarity	NPC234993
0.7912	Intermediate Similarity	NPC471219
0.7907	Intermediate Similarity	NPC132542
0.7895	Intermediate Similarity	NPC215700
0.7895	Intermediate Similarity	NPC470255
0.7889	Intermediate Similarity	NPC302360
0.7889	Intermediate Similarity	NPC32223
0.7889	Intermediate Similarity	NPC96055
0.7879	Intermediate Similarity	NPC475038
0.7879	Intermediate Similarity	NPC109195
0.7879	Intermediate Similarity	NPC162973
0.7872	Intermediate Similarity	NPC177641
0.7865	Intermediate Similarity	NPC471218
0.7864	Intermediate Similarity	NPC177047
0.7857	Intermediate Similarity	NPC324841
0.7857	Intermediate Similarity	NPC472826
0.7843	Intermediate Similarity	NPC88701
0.7843	Intermediate Similarity	NPC38948
0.7843	Intermediate Similarity	NPC306265
0.7843	Intermediate Similarity	NPC50124
0.7841	Intermediate Similarity	NPC469802
0.7835	Intermediate Similarity	NPC51499
0.7835	Intermediate Similarity	NPC205143
0.7812	Intermediate Similarity	NPC183012
0.7802	Intermediate Similarity	NPC471795
0.7802	Intermediate Similarity	NPC65661
0.78	Intermediate Similarity	NPC112009
0.78	Intermediate Similarity	NPC473523
0.78	Intermediate Similarity	NPC474124
0.78	Intermediate Similarity	NPC171014
0.78	Intermediate Similarity	NPC180204
0.7789	Intermediate Similarity	NPC472871
0.7778	Intermediate Similarity	NPC57370
0.7778	Intermediate Similarity	NPC295110
0.7778	Intermediate Similarity	NPC222875
0.7778	Intermediate Similarity	NPC268829
0.7778	Intermediate Similarity	NPC25177
0.7778	Intermediate Similarity	NPC247701
0.7767	Intermediate Similarity	NPC206618
0.7767	Intermediate Similarity	NPC475586
0.7765	Intermediate Similarity	NPC22134
0.7765	Intermediate Similarity	NPC71152
0.7755	Intermediate Similarity	NPC325229
0.7755	Intermediate Similarity	NPC92275
0.7755	Intermediate Similarity	NPC275086
0.7755	Intermediate Similarity	NPC247233
0.7755	Intermediate Similarity	NPC473154
0.7753	Intermediate Similarity	NPC142163
0.7745	Intermediate Similarity	NPC472820
0.7745	Intermediate Similarity	NPC43063
0.7745	Intermediate Similarity	NPC301666
0.7745	Intermediate Similarity	NPC79298
0.7742	Intermediate Similarity	NPC104560
0.7742	Intermediate Similarity	NPC291665
0.7742	Intermediate Similarity	NPC472810
0.7742	Intermediate Similarity	NPC472809
0.7742	Intermediate Similarity	NPC473879
0.7736	Intermediate Similarity	NPC147912
0.7736	Intermediate Similarity	NPC67259
0.7732	Intermediate Similarity	NPC190713
0.7732	Intermediate Similarity	NPC209297
0.7732	Intermediate Similarity	NPC471903
0.7732	Intermediate Similarity	NPC29952
0.7732	Intermediate Similarity	NPC472995
0.7732	Intermediate Similarity	NPC475380
0.7732	Intermediate Similarity	NPC57664
0.7727	Intermediate Similarity	NPC242767
0.7723	Intermediate Similarity	NPC473543
0.7717	Intermediate Similarity	NPC329692
0.7714	Intermediate Similarity	NPC470025
0.7714	Intermediate Similarity	NPC476801
0.7714	Intermediate Similarity	NPC328074
0.7714	Intermediate Similarity	NPC470063
0.7714	Intermediate Similarity	NPC321272
0.7714	Intermediate Similarity	NPC317460
0.7708	Intermediate Similarity	NPC279410
0.7708	Intermediate Similarity	NPC119562
0.7708	Intermediate Similarity	NPC472416
0.7708	Intermediate Similarity	NPC38830
0.7708	Intermediate Similarity	NPC140277
0.7708	Intermediate Similarity	NPC472360
0.7701	Intermediate Similarity	NPC189206

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 NPC82876 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	172
0.1-0.2	1458
0.2-0.3	3750
0.3-0.4	2415
0.4-0.5	901
0.5-0.6	241
0.6-0.7	199
0.7-0.8	13
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8316	Intermediate Similarity	NPD4225	Approved
0.7778	Intermediate Similarity	NPD5344	Discontinued
0.7755	Intermediate Similarity	NPD7638	Approved
0.7677	Intermediate Similarity	NPD7640	Approved
0.7677	Intermediate Similarity	NPD7639	Approved
0.7593	Intermediate Similarity	NPD7115	Discovery
0.75	Intermediate Similarity	NPD6648	Approved
0.7473	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7748	Approved
0.7297	Intermediate Similarity	NPD7516	Approved
0.7234	Intermediate Similarity	NPD1694	Approved
0.7207	Intermediate Similarity	NPD7328	Approved
0.7207	Intermediate Similarity	NPD7327	Approved
0.7196	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6686	Approved
0.7168	Intermediate Similarity	NPD7503	Approved
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7129	Intermediate Similarity	NPD7902	Approved
0.7113	Intermediate Similarity	NPD6051	Approved
0.7083	Intermediate Similarity	NPD3573	Approved
0.708	Intermediate Similarity	NPD8294	Approved
0.708	Intermediate Similarity	NPD8377	Approved
0.7075	Intermediate Similarity	NPD5697	Approved
0.7064	Intermediate Similarity	NPD8297	Approved
0.7019	Intermediate Similarity	NPD7632	Discontinued
0.7018	Intermediate Similarity	NPD8296	Approved
0.7018	Intermediate Similarity	NPD8378	Approved
0.7018	Intermediate Similarity	NPD8033	Approved
0.7018	Intermediate Similarity	NPD8335	Approved
0.7018	Intermediate Similarity	NPD8380	Approved
0.7018	Intermediate Similarity	NPD8379	Approved
0.7009	Intermediate Similarity	NPD6011	Approved
0.7009	Intermediate Similarity	NPD6881	Approved
0.7009	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6899	Approved
0.7	Intermediate Similarity	NPD4632	Approved
0.6944	Remote Similarity	NPD6012	Approved
0.6944	Remote Similarity	NPD6013	Approved
0.6944	Remote Similarity	NPD6014	Approved
0.6916	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7525	Registered
0.6881	Remote Similarity	NPD7102	Approved
0.6881	Remote Similarity	NPD7290	Approved
0.6881	Remote Similarity	NPD6883	Approved
0.6869	Remote Similarity	NPD7838	Discovery
0.6832	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7900	Approved
0.6822	Remote Similarity	NPD7128	Approved
0.6822	Remote Similarity	NPD5739	Approved
0.6822	Remote Similarity	NPD6675	Approved
0.6822	Remote Similarity	NPD6402	Approved
0.6818	Remote Similarity	NPD6869	Approved
0.6818	Remote Similarity	NPD8130	Phase 1
0.6818	Remote Similarity	NPD6847	Approved
0.6818	Remote Similarity	NPD6650	Approved
0.6818	Remote Similarity	NPD6617	Approved
0.6818	Remote Similarity	NPD6649	Approved
0.6804	Remote Similarity	NPD3618	Phase 1
0.68	Remote Similarity	NPD6079	Approved
0.6783	Remote Similarity	NPD6319	Approved
0.678	Remote Similarity	NPD7507	Approved
0.6774	Remote Similarity	NPD7645	Phase 2
0.6774	Remote Similarity	NPD4195	Approved
0.6759	Remote Similarity	NPD5701	Approved
0.6757	Remote Similarity	NPD6882	Approved
0.6735	Remote Similarity	NPD7524	Approved
0.6733	Remote Similarity	NPD6399	Phase 3
0.6699	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5222	Approved
0.6699	Remote Similarity	NPD5221	Approved
0.6698	Remote Similarity	NPD5211	Phase 2
0.6697	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6636	Remote Similarity	NPD6373	Approved
0.6636	Remote Similarity	NPD6372	Approved
0.6635	Remote Similarity	NPD5173	Approved
0.6635	Remote Similarity	NPD6083	Phase 2
0.6635	Remote Similarity	NPD6084	Phase 2
0.6634	Remote Similarity	NPD5693	Phase 1
0.6633	Remote Similarity	NPD5330	Approved
0.6633	Remote Similarity	NPD7146	Approved
0.6633	Remote Similarity	NPD6409	Approved
0.6633	Remote Similarity	NPD6684	Approved
0.6633	Remote Similarity	NPD7521	Approved
0.6633	Remote Similarity	NPD7334	Approved
0.6628	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7319	Approved
0.6604	Remote Similarity	NPD4159	Approved
0.6604	Remote Similarity	NPD5223	Approved
0.6602	Remote Similarity	NPD5695	Phase 3
0.66	Remote Similarity	NPD5328	Approved
0.6598	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD5983	Phase 2
0.6574	Remote Similarity	NPD5141	Approved
0.6571	Remote Similarity	NPD5696	Approved
0.6571	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4202	Approved
0.6542	Remote Similarity	NPD5226	Approved
0.6542	Remote Similarity	NPD5225	Approved
0.6542	Remote Similarity	NPD5224	Approved
0.6542	Remote Similarity	NPD4633	Approved
0.6535	Remote Similarity	NPD46	Approved
0.6535	Remote Similarity	NPD6698	Approved
0.6535	Remote Similarity	NPD5785	Approved
0.6522	Remote Similarity	NPD6317	Approved
0.6518	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6903	Approved
0.65	Remote Similarity	NPD5737	Approved
0.65	Remote Similarity	NPD6672	Approved
0.6481	Remote Similarity	NPD5175	Approved
0.6481	Remote Similarity	NPD5174	Approved
0.6476	Remote Similarity	NPD4755	Approved
0.6471	Remote Similarity	NPD7604	Phase 2
0.6471	Remote Similarity	NPD8035	Phase 2
0.6471	Remote Similarity	NPD7637	Suspended
0.6471	Remote Similarity	NPD8034	Phase 2
0.6466	Remote Similarity	NPD6335	Approved
0.6466	Remote Similarity	NPD6313	Approved
0.6466	Remote Similarity	NPD6314	Approved
0.6465	Remote Similarity	NPD4623	Approved
0.6465	Remote Similarity	NPD4519	Discontinued
0.6465	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6933	Approved
0.6452	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD6274	Approved
0.6435	Remote Similarity	NPD6868	Approved
0.6429	Remote Similarity	NPD3665	Phase 1
0.6429	Remote Similarity	NPD3666	Approved
0.6429	Remote Similarity	NPD4634	Approved
0.6429	Remote Similarity	NPD3133	Approved
0.6417	Remote Similarity	NPD7492	Approved
0.6415	Remote Similarity	NPD5290	Discontinued
0.641	Remote Similarity	NPD7100	Approved
0.641	Remote Similarity	NPD7101	Approved
0.6392	Remote Similarity	NPD5209	Approved
0.6392	Remote Similarity	NPD3667	Approved
0.6381	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD4697	Phase 3
0.6364	Remote Similarity	NPD6336	Discontinued
0.6364	Remote Similarity	NPD6008	Approved
0.6364	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6616	Approved
0.6356	Remote Similarity	NPD6054	Approved
0.6355	Remote Similarity	NPD4700	Approved
0.6354	Remote Similarity	NPD4695	Discontinued
0.6344	Remote Similarity	NPD7339	Approved
0.6344	Remote Similarity	NPD8264	Approved
0.6344	Remote Similarity	NPD6942	Approved
0.6339	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD6695	Phase 3
0.6311	Remote Similarity	NPD6411	Approved
0.6311	Remote Similarity	NPD5281	Approved
0.6311	Remote Similarity	NPD5284	Approved
0.6311	Remote Similarity	NPD7078	Approved
0.6306	Remote Similarity	NPD6412	Phase 2
0.6303	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD6015	Approved
0.6303	Remote Similarity	NPD6921	Approved
0.6303	Remote Similarity	NPD6016	Approved
0.6286	Remote Similarity	NPD5210	Approved
0.6286	Remote Similarity	NPD4629	Approved
0.6286	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6371	Approved
0.6275	Remote Similarity	NPD6904	Approved
0.6275	Remote Similarity	NPD6673	Approved
0.6275	Remote Similarity	NPD6080	Approved
0.6275	Remote Similarity	NPD4753	Phase 2
0.6263	Remote Similarity	NPD4786	Approved
0.6263	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD8133	Approved
0.626	Remote Similarity	NPD7736	Approved
0.625	Remote Similarity	NPD5779	Approved
0.625	Remote Similarity	NPD4730	Approved
0.625	Remote Similarity	NPD5988	Approved
0.625	Remote Similarity	NPD6370	Approved
0.625	Remote Similarity	NPD4729	Approved
0.625	Remote Similarity	NPD5778	Approved
0.6239	Remote Similarity	NPD4198	Discontinued
0.6238	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6924	Approved
0.6237	Remote Similarity	NPD6926	Approved
0.6224	Remote Similarity	NPD4221	Approved
0.6224	Remote Similarity	NPD4223	Phase 3
0.6198	Remote Similarity	NPD8328	Phase 3
0.619	Remote Similarity	NPD6001	Approved
0.6182	Remote Similarity	NPD4754	Approved
0.6176	Remote Similarity	NPD5208	Approved
0.617	Remote Similarity	NPD8039	Approved
0.6161	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD5694	Approved
0.6146	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.614	Remote Similarity	NPD5135	Approved
0.614	Remote Similarity	NPD5249	Phase 3

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