NPASS Compound

Structure

NPC255787 OpenBabel07101718292D 31 34 0 0 1 0 0 0 0 0999 V2000 -2.5981 -2.5000 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 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 0.5000 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 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 -5.0029 -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 -1.7321 3.0000 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 -3.4641 -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 -3.4641 -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 1 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 -1.5000 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 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 -2.5981 3.5000 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 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 23 1 0 0 0 0 7 9 1 0 0 0 0 7 18 1 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 22 1 0 0 0 0 10 29 1 0 0 0 0 11 16 1 0 0 0 0 11 17 2 0 0 0 0 12 15 2 0 0 0 0 12 19 1 0 0 0 0 13 25 2 0 0 0 0 13 30 1 0 0 0 0 14 26 2 0 0 0 0 14 31 1 0 0 0 0 15 17 1 0 0 0 0 16 19 2 0 0 0 0 16 23 1 0 0 0 0 17 29 1 0 0 0 0 18 23 1 1 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 6 0 0 0 21 24 1 1 0 0 0 21 31 1 0 0 0 0 22 24 1 0 0 0 0 23 24 1 6 0 0 0 24 28 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	430.2
Volume:	435.147
LogP:	3.111
LogD:	2.327
LogS:	-4.527
# Rotatable Bonds:	4
TPSA:	106.2
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.703
Synthetic Accessibility Score:	4.629
Fsp3:	0.583
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:	-4.757
MDCK Permeability:	3.26917834172491e-05
Pgp-inhibitor:	0.88
Pgp-substrate:	0.644
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.285

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.394
Plasma Protein Binding (PPB):	86.07454681396484%
Volume Distribution (VD):	2.338
Pgp-substrate:	17.909393310546875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.051
CYP2C19-substrate:	0.681
CYP2C9-inhibitor:	0.267
CYP2C9-substrate:	0.44
CYP2D6-inhibitor:	0.111
CYP2D6-substrate:	0.231
CYP3A4-inhibitor:	0.363
CYP3A4-substrate:	0.511

ADMET: Excretion

Clearance (CL):	2.166
Half-life (T1/2):	0.063

ADMET: Toxicity

hERG Blockers:	0.158
Human Hepatotoxicity (H-HT):	0.338
Drug-inuced Liver Injury (DILI):	0.556
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.389
Maximum Recommended Daily Dose:	0.728
Skin Sensitization:	0.093
Carcinogencity:	0.466
Eye Corrosion:	0.004
Eye Irritation:	0.018
Respiratory Toxicity:	0.807

Download Data

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

Natural Product: NPC255787

Natural Product ID:	NPC255787
*Common Name:**	1Alpha,6Alpha-Diacetoxy-5Alpha,7Beta-Dihydroxy-14-Methylvoucapane-8(14),9(11)-Diene
IUPAC Name:	[(1S,4aR,5S,6R,11bS)-5-acetyloxy-4a,6-dihydroxy-4,4,7,11b-tetramethyl-2,3,5,6-tetrahydro-1H-naphtho[2,1-f][1]benzofuran-1-yl] acetate
Synonyms:
Standard InCHIKey:	QBYMPSZQBDARHI-ZJLRUGLKSA-N
Standard InCHI:	InChI=1S/C24H30O7/c1-12-15-8-10-29-17(15)11-16-19(12)20(27)21(31-14(3)26)24(28)22(4,5)9-7-18(23(16,24)6)30-13(2)25/h8,10-11,18,20-21,27-28H,7,9H2,1-6H3/t18-,20+,21-,23-,24+/m0/s1
SMILES:	CC(=O)O[C@H]1[C@H](O)c2c(C)c3ccoc3cc2[C@@]2([C@]1(O)C(C)(C)CC[C@@H]2OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386705
PubChem CID:	71725695
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes 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
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678648]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[23806110]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[24303808]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14392	Caesalpinia minax	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14392	Caesalpinia minax	Species	Fabaceae	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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	50000.0	nM	PMID[542207]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	50000.0	nM	PMID[542207]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	50000.0	nM	PMID[542207]
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	50000.0	nM	PMID[542207]

☑ 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 NPC255787 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	354
0.1-0.2	1400
0.2-0.3	2851
0.3-0.4	6177
0.4-0.5	10967
0.5-0.6	5781
0.6-0.7	5682
0.7-0.8	8563
0.8-0.85	853
0.85-0.9	62
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9745	High Similarity	NPC308156
0.9623	High Similarity	NPC291742
0.9551	High Similarity	NPC123153
0.9437	High Similarity	NPC41689
0.9367	High Similarity	NPC472299
0.9119	High Similarity	NPC194499
0.9068	High Similarity	NPC79571
0.9059	High Similarity	NPC472662
0.9059	High Similarity	NPC472663
0.9051	High Similarity	NPC44606
0.9006	High Similarity	NPC8389
0.9	High Similarity	NPC88007
0.8931	High Similarity	NPC10429
0.8909	High Similarity	NPC296558
0.8896	High Similarity	NPC288602
0.8896	High Similarity	NPC283209
0.8896	High Similarity	NPC88841
0.8882	High Similarity	NPC7059
0.8882	High Similarity	NPC195954
0.8868	High Similarity	NPC294511
0.8868	High Similarity	NPC121615
0.8861	High Similarity	NPC228842
0.8834	High Similarity	NPC68848
0.8834	High Similarity	NPC18986
0.8834	High Similarity	NPC188649
0.8797	High Similarity	NPC95526
0.8788	High Similarity	NPC121995
0.8788	High Similarity	NPC277618
0.878	High Similarity	NPC285567
0.8742	High Similarity	NPC212257
0.8734	High Similarity	NPC66991
0.8671	High Similarity	NPC286038
0.8667	High Similarity	NPC469889
0.8662	High Similarity	NPC290038
0.8659	High Similarity	NPC287559
0.8659	High Similarity	NPC218818
0.8659	High Similarity	NPC4950
0.8655	High Similarity	NPC472661
0.865	High Similarity	NPC304692
0.8631	High Similarity	NPC473094
0.8631	High Similarity	NPC472660
0.8625	High Similarity	NPC472298
0.8614	High Similarity	NPC56358
0.8606	High Similarity	NPC239270
0.8606	High Similarity	NPC470810
0.8606	High Similarity	NPC303210
0.8606	High Similarity	NPC95472
0.8598	High Similarity	NPC158542
0.8589	High Similarity	NPC41880
0.8589	High Similarity	NPC104736
0.8588	High Similarity	NPC472620
0.858	High Similarity	NPC473096
0.858	High Similarity	NPC472619
0.858	High Similarity	NPC473095
0.8563	High Similarity	NPC100849
0.8562	High Similarity	NPC125182
0.8562	High Similarity	NPC69647
0.8555	High Similarity	NPC104682
0.8554	High Similarity	NPC14822
0.8554	High Similarity	NPC269117
0.8553	High Similarity	NPC71821
0.8547	High Similarity	NPC324220
0.8547	High Similarity	NPC312630
0.8545	High Similarity	NPC239118
0.8537	High Similarity	NPC478223
0.8529	High Similarity	NPC313304
0.8521	High Similarity	NPC472622
0.8521	High Similarity	NPC118086
0.8512	High Similarity	NPC310572
0.8512	High Similarity	NPC270312
0.8494	Intermediate Similarity	NPC169
0.8494	Intermediate Similarity	NPC49009
0.8488	Intermediate Similarity	NPC294149
0.8485	Intermediate Similarity	NPC140952
0.8485	Intermediate Similarity	NPC10051
0.8485	Intermediate Similarity	NPC474611
0.8485	Intermediate Similarity	NPC143328
0.8485	Intermediate Similarity	NPC299094
0.8476	Intermediate Similarity	NPC478161
0.8476	Intermediate Similarity	NPC478159
0.8476	Intermediate Similarity	NPC300757
0.8476	Intermediate Similarity	NPC180901
0.8471	Intermediate Similarity	NPC475237
0.8471	Intermediate Similarity	NPC475641
0.8462	Intermediate Similarity	NPC263212
0.8462	Intermediate Similarity	NPC53640
0.8462	Intermediate Similarity	NPC472621
0.8443	Intermediate Similarity	NPC45124
0.8443	Intermediate Similarity	NPC475039
0.8443	Intermediate Similarity	NPC92589
0.8443	Intermediate Similarity	NPC30655
0.8443	Intermediate Similarity	NPC476035
0.8443	Intermediate Similarity	NPC74854
0.8443	Intermediate Similarity	NPC14499
0.8443	Intermediate Similarity	NPC117985
0.8438	Intermediate Similarity	NPC255414
0.8434	Intermediate Similarity	NPC477692
0.8434	Intermediate Similarity	NPC470339
0.8434	Intermediate Similarity	NPC226287
0.843	Intermediate Similarity	NPC98776
0.8424	Intermediate Similarity	NPC81405
0.8421	Intermediate Similarity	NPC52598
0.8421	Intermediate Similarity	NPC51404
0.8415	Intermediate Similarity	NPC84721
0.8412	Intermediate Similarity	NPC44602
0.8412	Intermediate Similarity	NPC150131
0.8405	Intermediate Similarity	NPC48671
0.8402	Intermediate Similarity	NPC472784
0.8402	Intermediate Similarity	NPC136641
0.8393	Intermediate Similarity	NPC478229
0.8385	Intermediate Similarity	NPC14875
0.8383	Intermediate Similarity	NPC472055
0.8383	Intermediate Similarity	NPC21046
0.8382	Intermediate Similarity	NPC224165
0.8373	Intermediate Similarity	NPC269495
0.8373	Intermediate Similarity	NPC212967
0.8373	Intermediate Similarity	NPC164110
0.8373	Intermediate Similarity	NPC246647
0.8373	Intermediate Similarity	NPC270044
0.8373	Intermediate Similarity	NPC96342
0.8372	Intermediate Similarity	NPC472584
0.8365	Intermediate Similarity	NPC158871
0.8363	Intermediate Similarity	NPC294512
0.8363	Intermediate Similarity	NPC473202
0.8354	Intermediate Similarity	NPC114880
0.8354	Intermediate Similarity	NPC131121
0.8354	Intermediate Similarity	NPC263337
0.8354	Intermediate Similarity	NPC184053
0.8353	Intermediate Similarity	NPC43065
0.8353	Intermediate Similarity	NPC125465
0.8352	Intermediate Similarity	NPC475148
0.8352	Intermediate Similarity	NPC475656
0.8352	Intermediate Similarity	NPC228209
0.8344	Intermediate Similarity	NPC13282
0.8344	Intermediate Similarity	NPC225854
0.8343	Intermediate Similarity	NPC45943
0.8343	Intermediate Similarity	NPC205265
0.8343	Intermediate Similarity	NPC472281
0.8333	Intermediate Similarity	NPC295914
0.8333	Intermediate Similarity	NPC11062
0.8333	Intermediate Similarity	NPC478050
0.8333	Intermediate Similarity	NPC478222
0.8333	Intermediate Similarity	NPC211625
0.8333	Intermediate Similarity	NPC24761
0.8333	Intermediate Similarity	NPC107244
0.8333	Intermediate Similarity	NPC475233
0.8324	Intermediate Similarity	NPC184624
0.8323	Intermediate Similarity	NPC63918
0.8314	Intermediate Similarity	NPC120220
0.8314	Intermediate Similarity	NPC131866
0.8314	Intermediate Similarity	NPC298778
0.8314	Intermediate Similarity	NPC315306
0.8314	Intermediate Similarity	NPC313717
0.8313	Intermediate Similarity	NPC471451
0.8313	Intermediate Similarity	NPC5676
0.8313	Intermediate Similarity	NPC221992
0.8313	Intermediate Similarity	NPC260152
0.8313	Intermediate Similarity	NPC109765
0.8313	Intermediate Similarity	NPC471305
0.8313	Intermediate Similarity	NPC180924
0.8303	Intermediate Similarity	NPC62051
0.8303	Intermediate Similarity	NPC303950
0.8303	Intermediate Similarity	NPC179170
0.8295	Intermediate Similarity	NPC208069
0.8294	Intermediate Similarity	NPC472277
0.8293	Intermediate Similarity	NPC474772
0.8293	Intermediate Similarity	NPC474744
0.8293	Intermediate Similarity	NPC268905
0.8293	Intermediate Similarity	NPC474417
0.8293	Intermediate Similarity	NPC149526
0.8293	Intermediate Similarity	NPC472423
0.8284	Intermediate Similarity	NPC472402
0.8284	Intermediate Similarity	NPC62692
0.8284	Intermediate Similarity	NPC61967
0.8284	Intermediate Similarity	NPC27541
0.8284	Intermediate Similarity	NPC473022
0.8284	Intermediate Similarity	NPC144843
0.8284	Intermediate Similarity	NPC126984
0.8276	Intermediate Similarity	NPC68381
0.8276	Intermediate Similarity	NPC53917
0.8276	Intermediate Similarity	NPC193377
0.8276	Intermediate Similarity	NPC472665
0.8274	Intermediate Similarity	NPC328102
0.8274	Intermediate Similarity	NPC472618
0.8274	Intermediate Similarity	NPC470792
0.8274	Intermediate Similarity	NPC47623
0.8274	Intermediate Similarity	NPC476283
0.8274	Intermediate Similarity	NPC200782
0.8274	Intermediate Similarity	NPC220582
0.8274	Intermediate Similarity	NPC304839
0.8266	Intermediate Similarity	NPC471920
0.8266	Intermediate Similarity	NPC312006
0.8266	Intermediate Similarity	NPC148185
0.8266	Intermediate Similarity	NPC129930
0.8266	Intermediate Similarity	NPC114550
0.8266	Intermediate Similarity	NPC292712
0.8266	Intermediate Similarity	NPC473113
0.8266	Intermediate Similarity	NPC247964
0.8266	Intermediate Similarity	NPC307286
0.8266	Intermediate Similarity	NPC471922

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 NPC255787 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	862
0.2-0.3	1661
0.3-0.4	2485
0.4-0.5	2054
0.5-0.6	1119
0.6-0.7	464
0.7-0.8	185
0.8-0.85	11
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.858	High Similarity	NPD5844	Phase 1
0.8471	Intermediate Similarity	NPD4628	Phase 3
0.843	Intermediate Similarity	NPD6559	Discontinued
0.84	Intermediate Similarity	NPD8434	Phase 2
0.8084	Intermediate Similarity	NPD7819	Suspended
0.807	Intermediate Similarity	NPD6232	Discontinued
0.8063	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD7473	Discontinued
0.8024	Intermediate Similarity	NPD6801	Discontinued
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.7988	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD3226	Approved
0.7941	Intermediate Similarity	NPD7075	Discontinued
0.7941	Intermediate Similarity	NPD3749	Approved
0.7939	Intermediate Similarity	NPD920	Approved
0.7895	Intermediate Similarity	NPD919	Approved
0.7879	Intermediate Similarity	NPD6273	Approved
0.7844	Intermediate Similarity	NPD7458	Discontinued
0.7826	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD2533	Approved
0.7818	Intermediate Similarity	NPD2532	Approved
0.7818	Intermediate Similarity	NPD2534	Approved
0.7814	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD1934	Approved
0.7798	Intermediate Similarity	NPD4380	Phase 2
0.7791	Intermediate Similarity	NPD7003	Approved
0.7784	Intermediate Similarity	NPD3818	Discontinued
0.7765	Intermediate Similarity	NPD1465	Phase 2
0.7765	Intermediate Similarity	NPD5761	Phase 2
0.7765	Intermediate Similarity	NPD5760	Phase 2
0.7751	Intermediate Similarity	NPD7411	Suspended
0.7746	Intermediate Similarity	NPD5494	Approved
0.7735	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD8313	Approved
0.7722	Intermediate Similarity	NPD8312	Approved
0.7719	Intermediate Similarity	NPD3817	Phase 2
0.7716	Intermediate Similarity	NPD2346	Discontinued
0.7711	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD6765	Approved
0.7709	Intermediate Similarity	NPD6764	Approved
0.7706	Intermediate Similarity	NPD37	Approved
0.7705	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7701	Intermediate Similarity	NPD7199	Phase 2
0.7697	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3750	Approved
0.7674	Intermediate Similarity	NPD3882	Suspended
0.7674	Intermediate Similarity	NPD4967	Phase 2
0.7674	Intermediate Similarity	NPD4966	Approved
0.7674	Intermediate Similarity	NPD4965	Approved
0.767	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6166	Phase 2
0.767	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6799	Approved
0.763	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD8127	Discontinued
0.76	Intermediate Similarity	NPD1247	Approved
0.7586	Intermediate Similarity	NPD6234	Discontinued
0.7584	Intermediate Similarity	NPD7177	Discontinued
0.7584	Intermediate Similarity	NPD3751	Discontinued
0.7576	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD7768	Phase 2
0.7571	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD2801	Approved
0.7557	Intermediate Similarity	NPD7229	Phase 3
0.7545	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD6785	Approved
0.7541	Intermediate Similarity	NPD6784	Approved
0.7515	Intermediate Similarity	NPD1243	Approved
0.7515	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD7074	Phase 3
0.7485	Intermediate Similarity	NPD3748	Approved
0.7458	Intermediate Similarity	NPD3787	Discontinued
0.7457	Intermediate Similarity	NPD8455	Phase 2
0.7455	Intermediate Similarity	NPD1549	Phase 2
0.7444	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7054	Approved
0.744	Intermediate Similarity	NPD1511	Approved
0.7439	Intermediate Similarity	NPD2796	Approved
0.7439	Intermediate Similarity	NPD6100	Approved
0.7439	Intermediate Similarity	NPD2935	Discontinued
0.7439	Intermediate Similarity	NPD6099	Approved
0.7439	Intermediate Similarity	NPD1551	Phase 2
0.7438	Intermediate Similarity	NPD3764	Approved
0.7425	Intermediate Similarity	NPD6190	Approved
0.7412	Intermediate Similarity	NPD5403	Approved
0.741	Intermediate Similarity	NPD2800	Approved
0.7409	Intermediate Similarity	NPD7435	Discontinued
0.7403	Intermediate Similarity	NPD7472	Approved
0.7394	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2344	Approved
0.7389	Intermediate Similarity	NPD7228	Approved
0.7389	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD2799	Discontinued
0.7378	Intermediate Similarity	NPD7033	Discontinued
0.7377	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD6797	Phase 2
0.7353	Intermediate Similarity	NPD1512	Approved
0.7349	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD4060	Phase 1
0.7344	Intermediate Similarity	NPD6781	Approved
0.7344	Intermediate Similarity	NPD6782	Approved
0.7344	Intermediate Similarity	NPD6777	Approved
0.7344	Intermediate Similarity	NPD6779	Approved
0.7344	Intermediate Similarity	NPD6778	Approved
0.7344	Intermediate Similarity	NPD6776	Approved
0.7344	Intermediate Similarity	NPD6780	Approved
0.7333	Intermediate Similarity	NPD2438	Suspended
0.7329	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6798	Discontinued
0.7329	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7322	Intermediate Similarity	NPD7251	Discontinued
0.7318	Intermediate Similarity	NPD3926	Phase 2
0.7314	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD8404	Phase 2
0.731	Intermediate Similarity	NPD8151	Discontinued
0.7305	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6355	Discontinued
0.7294	Intermediate Similarity	NPD5401	Approved
0.7283	Intermediate Similarity	NPD7808	Phase 3
0.7278	Intermediate Similarity	NPD1283	Approved
0.7273	Intermediate Similarity	NPD1510	Phase 2
0.7273	Intermediate Similarity	NPD4308	Phase 3
0.7268	Intermediate Similarity	NPD3057	Approved
0.7267	Intermediate Similarity	NPD7095	Approved
0.7263	Intermediate Similarity	NPD5710	Approved
0.7263	Intermediate Similarity	NPD5711	Approved
0.7256	Intermediate Similarity	NPD1607	Approved
0.7239	Intermediate Similarity	NPD2979	Phase 3
0.7239	Intermediate Similarity	NPD4140	Approved
0.7236	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD7783	Phase 2
0.7229	Intermediate Similarity	NPD5405	Approved
0.7229	Intermediate Similarity	NPD5404	Approved
0.7229	Intermediate Similarity	NPD5406	Approved
0.7229	Intermediate Similarity	NPD5408	Approved
0.7228	Intermediate Similarity	NPD7685	Pre-registration
0.7222	Intermediate Similarity	NPD2313	Discontinued
0.7219	Intermediate Similarity	NPD2309	Approved
0.7193	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6002	Phase 3
0.7186	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD6005	Phase 3
0.7186	Intermediate Similarity	NPD7874	Approved
0.7186	Intermediate Similarity	NPD6004	Phase 3
0.7186	Intermediate Similarity	NPD5763	Approved
0.7186	Intermediate Similarity	NPD5762	Approved
0.7182	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2972	Approved
0.7179	Intermediate Similarity	NPD3533	Approved
0.7178	Intermediate Similarity	NPD6233	Phase 2
0.7178	Intermediate Similarity	NPD8032	Phase 2
0.7169	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD4107	Approved
0.716	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4625	Phase 3
0.716	Intermediate Similarity	NPD8166	Discontinued
0.716	Intermediate Similarity	NPD4110	Phase 3
0.7152	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD7698	Approved
0.7143	Intermediate Similarity	NPD7697	Approved
0.7143	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD7390	Discontinued
0.7135	Intermediate Similarity	NPD7038	Approved
0.7135	Intermediate Similarity	NPD7039	Approved
0.7135	Intermediate Similarity	NPD7240	Approved
0.7134	Intermediate Similarity	NPD1240	Approved
0.7117	Intermediate Similarity	NPD3268	Approved
0.7107	Intermediate Similarity	NPD7870	Phase 2
0.7107	Intermediate Similarity	NPD7871	Phase 2
0.7101	Intermediate Similarity	NPD6674	Discontinued
0.7092	Intermediate Similarity	NPD2491	Approved
0.7092	Intermediate Similarity	NPD6823	Phase 2
0.7091	Intermediate Similarity	NPD230	Phase 1
0.7089	Intermediate Similarity	NPD1281	Approved
0.7085	Intermediate Similarity	NPD7701	Phase 2
0.7083	Intermediate Similarity	NPD1471	Phase 3
0.7083	Intermediate Similarity	NPD6535	Approved
0.7083	Intermediate Similarity	NPD6534	Approved
0.7076	Intermediate Similarity	NPD7236	Approved
0.7073	Intermediate Similarity	NPD4111	Phase 1
0.7073	Intermediate Similarity	NPD4665	Approved
0.7071	Intermediate Similarity	NPD7999	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