NPASS Compound

Structure

NPC277618 OpenBabel07101719252D 40 45 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 -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 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 -3.4641 1.0000 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 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 1 0 0 0 0 0 0 0 0 0 0.0000 4.0000 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 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 1 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 1.7321 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 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -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 0.8660 2.5000 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 2 32 1 0 0 0 0 3 32 1 0 0 0 0 4 33 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 10 15 2 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 22 2 0 0 0 0 13 22 1 0 0 0 0 14 23 2 0 0 0 0 15 23 1 0 0 0 0 16 19 2 0 0 0 0 16 24 1 0 0 0 0 17 32 1 0 0 0 0 18 33 1 0 0 0 0 19 38 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 0 0 0 0 21 1 1 1 0 0 0 21 24 1 0 0 0 0 21 27 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 26 2 0 0 0 0 25 27 1 0 0 0 0 25 33 1 6 0 0 0 26 38 1 0 0 0 0 27 28 1 0 0 0 0 28 29 1 0 0 0 0 28 39 1 0 0 0 0 29 34 1 0 0 0 0 29 40 1 0 0 0 0 30 35 2 0 0 0 0 30 39 1 0 0 0 0 31 36 2 0 0 0 0 31 40 1 0 0 0 0 32 34 1 0 0 0 0 33 34 1 0 0 0 0 34 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	542.27
Volume:	571.658
LogP:	6.298
LogD:	5.241
LogS:	-4.857
# Rotatable Bonds:	6
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	4.556
Fsp3:	0.471
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.883
MDCK Permeability:	1.8476173863746226e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.119
30% Bioavailability (F30%):	0.101

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	101.77759552001953%
Volume Distribution (VD):	2.217
Pgp-substrate:	3.6247000694274902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.139
CYP1A2-substrate:	0.134
CYP2C19-inhibitor:	0.79
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.573
CYP2C9-substrate:	0.452
CYP2D6-inhibitor:	0.713
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.793
CYP3A4-substrate:	0.213

ADMET: Excretion

Clearance (CL):	9.041
Half-life (T1/2):	0.153

ADMET: Toxicity

hERG Blockers:	0.836
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.961
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.144
Maximum Recommended Daily Dose:	0.018
Skin Sensitization:	0.17
Carcinogencity:	0.171
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.143

Download Data

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

Natural Product: NPC277618

Natural Product ID:	NPC277618
*Common Name:**	6Beta,7Beta-Dibenzoyloxyvouacapen-5Alpha-Ol
IUPAC Name:	[(4aR,5R,6R,6aS,7R,11aS,11bR)-5-benzoyloxy-4a-hydroxy-4,4,7,11b-tetramethyl-2,3,5,6,6a,7,11,11a-octahydro-1H-naphtho[2,1-f][1]benzofuran-6-yl] benzoate
Synonyms:
Standard InCHIKey:	ZLUDDZRRFBOSTI-RLZZOFBFSA-N
Standard InCHI:	InChI=1S/C34H38O6/c1-21-24-16-19-38-26(24)20-25-27(21)28(39-30(35)22-12-7-5-8-13-22)29(40-31(36)23-14-9-6-10-15-23)34(37)32(2,3)17-11-18-33(25,34)4/h5-10,12-16,19,21,25,27-29,37H,11,17-18,20H2,1-4H3/t21-,25-,27-,28+,29+,33+,34+/m0/s1
SMILES:	O=C(c1ccccc1)O[C@@H]1[C@H]2[C@@H](C)c3ccoc3C[C@@H]2[C@@]2([C@]([C@@H]1OC(=O)c1ccccc1)(O)C(C)(C)CCC2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095680
PubChem CID:	46861634
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
NPO32590	caesalpinia sp.	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20356735]

☑ 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
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	33900.0	nM	PMID[520304]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	19770.0	nM	PMID[520304]

☑ 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 NPC277618 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	352
0.1-0.2	1327
0.2-0.3	2642
0.3-0.4	5151
0.4-0.5	9969
0.5-0.6	8476
0.6-0.7	6700
0.7-0.8	7400
0.8-0.85	541
0.85-0.9	118
0.9-0.95	17
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.974	High Similarity	NPC8389
0.9677	High Similarity	NPC79571
0.961	High Similarity	NPC7059
0.9375	High Similarity	NPC296558
0.9359	High Similarity	NPC88007
0.9359	High Similarity	NPC194499
0.9236	High Similarity	NPC195954
0.9226	High Similarity	NPC121615
0.9226	High Similarity	NPC294511
0.9221	High Similarity	NPC228842
0.9221	High Similarity	NPC212257
0.9182	High Similarity	NPC68848
0.9074	High Similarity	NPC41689
0.9074	High Similarity	NPC310572
0.9062	High Similarity	NPC188649
0.9062	High Similarity	NPC18986
0.9026	High Similarity	NPC71821
0.9006	High Similarity	NPC285567
0.9006	High Similarity	NPC283209
0.9006	High Similarity	NPC288602
0.9006	High Similarity	NPC88841
0.8976	High Similarity	NPC56953
0.8976	High Similarity	NPC176413
0.8938	High Similarity	NPC474611
0.8931	High Similarity	NPC41880
0.8896	High Similarity	NPC121995
0.8882	High Similarity	NPC287559
0.8848	High Similarity	NPC118086
0.8827	High Similarity	NPC471003
0.8812	High Similarity	NPC104736
0.8795	High Similarity	NPC294512
0.8795	High Similarity	NPC475237
0.8795	High Similarity	NPC475641
0.879	High Similarity	NPC125182
0.879	High Similarity	NPC69647
0.8788	High Similarity	NPC291742
0.8788	High Similarity	NPC255787
0.8782	High Similarity	NPC255414
0.878	High Similarity	NPC308156
0.8773	High Similarity	NPC14499
0.8773	High Similarity	NPC476035
0.8773	High Similarity	NPC475039
0.8758	High Similarity	NPC304692
0.8735	High Similarity	NPC302392
0.8735	High Similarity	NPC88593
0.8727	High Similarity	NPC270312
0.872	High Similarity	NPC126984
0.872	High Similarity	NPC27541
0.872	High Similarity	NPC61967
0.872	High Similarity	NPC56358
0.872	High Similarity	NPC62692
0.8704	High Similarity	NPC123153
0.8701	High Similarity	NPC263337
0.8647	High Similarity	NPC11062
0.8642	High Similarity	NPC81405
0.8599	High Similarity	NPC281717
0.8589	High Similarity	NPC140952
0.8571	High Similarity	NPC302054
0.8571	High Similarity	NPC253201
0.8563	High Similarity	NPC160651
0.8554	High Similarity	NPC86800
0.8553	High Similarity	NPC211625
0.8544	High Similarity	NPC301556
0.8544	High Similarity	NPC270590
0.8544	High Similarity	NPC92293
0.8544	High Similarity	NPC471101
0.8544	High Similarity	NPC266265
0.8535	High Similarity	NPC5676
0.8509	High Similarity	NPC268905
0.8509	High Similarity	NPC48671
0.8509	High Similarity	NPC472672
0.8506	High Similarity	NPC202260
0.85	High Similarity	NPC327962
0.8494	Intermediate Similarity	NPC276735
0.8494	Intermediate Similarity	NPC469849
0.8494	Intermediate Similarity	NPC470182
0.8485	Intermediate Similarity	NPC82851
0.8485	Intermediate Similarity	NPC470792
0.8485	Intermediate Similarity	NPC200782
0.8476	Intermediate Similarity	NPC84349
0.8466	Intermediate Similarity	NPC471102
0.8462	Intermediate Similarity	NPC121158
0.8457	Intermediate Similarity	NPC98206
0.8457	Intermediate Similarity	NPC237259
0.8457	Intermediate Similarity	NPC34421
0.8443	Intermediate Similarity	NPC475779
0.8443	Intermediate Similarity	NPC470875
0.8434	Intermediate Similarity	NPC469338
0.8434	Intermediate Similarity	NPC472773
0.8434	Intermediate Similarity	NPC292389
0.8428	Intermediate Similarity	NPC286038
0.8428	Intermediate Similarity	NPC216755
0.8424	Intermediate Similarity	NPC472299
0.8415	Intermediate Similarity	NPC299038
0.8408	Intermediate Similarity	NPC25768
0.8408	Intermediate Similarity	NPC95810
0.8408	Intermediate Similarity	NPC57628
0.8408	Intermediate Similarity	NPC188865
0.8408	Intermediate Similarity	NPC476974
0.8408	Intermediate Similarity	NPC472569
0.8408	Intermediate Similarity	NPC472573
0.8408	Intermediate Similarity	NPC475122
0.8408	Intermediate Similarity	NPC163719
0.8408	Intermediate Similarity	NPC11685
0.8408	Intermediate Similarity	NPC70716
0.8408	Intermediate Similarity	NPC95265
0.8408	Intermediate Similarity	NPC125106
0.8408	Intermediate Similarity	NPC472570
0.8405	Intermediate Similarity	NPC25351
0.8405	Intermediate Similarity	NPC476262
0.8405	Intermediate Similarity	NPC296807
0.8405	Intermediate Similarity	NPC155939
0.8405	Intermediate Similarity	NPC141538
0.8405	Intermediate Similarity	NPC469771
0.8402	Intermediate Similarity	NPC177362
0.8395	Intermediate Similarity	NPC246164
0.8395	Intermediate Similarity	NPC476201
0.8393	Intermediate Similarity	NPC173516
0.8393	Intermediate Similarity	NPC472282
0.8385	Intermediate Similarity	NPC477905
0.8383	Intermediate Similarity	NPC470940
0.8383	Intermediate Similarity	NPC276551
0.8377	Intermediate Similarity	NPC307401
0.8375	Intermediate Similarity	NPC66991
0.8375	Intermediate Similarity	NPC477483
0.8375	Intermediate Similarity	NPC325032
0.8373	Intermediate Similarity	NPC329938
0.8373	Intermediate Similarity	NPC472771
0.8372	Intermediate Similarity	NPC472665
0.8364	Intermediate Similarity	NPC472671
0.8364	Intermediate Similarity	NPC475967
0.8354	Intermediate Similarity	NPC470159
0.8354	Intermediate Similarity	NPC70403
0.8354	Intermediate Similarity	NPC200471
0.8354	Intermediate Similarity	NPC174982
0.8354	Intermediate Similarity	NPC177940
0.8354	Intermediate Similarity	NPC472807
0.8354	Intermediate Similarity	NPC472571
0.8354	Intermediate Similarity	NPC469349
0.8354	Intermediate Similarity	NPC158663
0.8354	Intermediate Similarity	NPC96903
0.8354	Intermediate Similarity	NPC171525
0.8354	Intermediate Similarity	NPC476973
0.8354	Intermediate Similarity	NPC470157
0.8354	Intermediate Similarity	NPC473088
0.8354	Intermediate Similarity	NPC29704
0.8354	Intermediate Similarity	NPC472572
0.8354	Intermediate Similarity	NPC472575
0.8354	Intermediate Similarity	NPC184817
0.8354	Intermediate Similarity	NPC471104
0.8354	Intermediate Similarity	NPC472568
0.8353	Intermediate Similarity	NPC202428
0.8353	Intermediate Similarity	NPC266545
0.8344	Intermediate Similarity	NPC147217
0.8344	Intermediate Similarity	NPC191082
0.8344	Intermediate Similarity	NPC246480
0.8344	Intermediate Similarity	NPC139067
0.8344	Intermediate Similarity	NPC177340
0.8344	Intermediate Similarity	NPC475429
0.8344	Intermediate Similarity	NPC473673
0.8344	Intermediate Similarity	NPC270498
0.8344	Intermediate Similarity	NPC114880
0.8344	Intermediate Similarity	NPC282445
0.8343	Intermediate Similarity	NPC200726
0.8343	Intermediate Similarity	NPC471397
0.8343	Intermediate Similarity	NPC271235
0.8333	Intermediate Similarity	NPC158333
0.8333	Intermediate Similarity	NPC472030
0.8333	Intermediate Similarity	NPC265395
0.8333	Intermediate Similarity	NPC237549
0.8333	Intermediate Similarity	NPC257213
0.8333	Intermediate Similarity	NPC77719
0.8333	Intermediate Similarity	NPC242262
0.8333	Intermediate Similarity	NPC256142
0.8333	Intermediate Similarity	NPC304876
0.8333	Intermediate Similarity	NPC472005
0.8333	Intermediate Similarity	NPC472141
0.8333	Intermediate Similarity	NPC45943
0.8333	Intermediate Similarity	NPC119252
0.8333	Intermediate Similarity	NPC1173
0.8333	Intermediate Similarity	NPC473414
0.8333	Intermediate Similarity	NPC249471
0.8333	Intermediate Similarity	NPC224491
0.8333	Intermediate Similarity	NPC472022
0.8323	Intermediate Similarity	NPC134254
0.8323	Intermediate Similarity	NPC39986
0.8323	Intermediate Similarity	NPC302369
0.8323	Intermediate Similarity	NPC476197
0.8323	Intermediate Similarity	NPC477405
0.8323	Intermediate Similarity	NPC234494
0.8323	Intermediate Similarity	NPC469889
0.8313	Intermediate Similarity	NPC471174
0.8313	Intermediate Similarity	NPC473215
0.8313	Intermediate Similarity	NPC472653
0.8313	Intermediate Similarity	NPC335761
0.8304	Intermediate Similarity	NPC180768
0.8304	Intermediate Similarity	NPC472803
0.8303	Intermediate Similarity	NPC249021
0.8303	Intermediate Similarity	NPC167142
0.8303	Intermediate Similarity	NPC214495

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 NPC277618 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	302
0.1-0.2	827
0.2-0.3	1485
0.3-0.4	2481
0.4-0.5	2227
0.5-0.6	1223
0.6-0.7	460
0.7-0.8	142
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8605	High Similarity	NPD8434	Phase 2
0.8113	Intermediate Similarity	NPD4628	Phase 3
0.8049	Intermediate Similarity	NPD7458	Discontinued
0.7866	Intermediate Similarity	NPD6273	Approved
0.7857	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5761	Phase 2
0.7857	Intermediate Similarity	NPD7819	Suspended
0.7857	Intermediate Similarity	NPD5760	Phase 2
0.7829	Intermediate Similarity	NPD5844	Phase 1
0.7826	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD8313	Approved
0.7809	Intermediate Similarity	NPD8312	Approved
0.7805	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD6764	Approved
0.7797	Intermediate Similarity	NPD6765	Approved
0.7791	Intermediate Similarity	NPD8127	Discontinued
0.7784	Intermediate Similarity	NPD6599	Discontinued
0.7778	Intermediate Similarity	NPD7003	Approved
0.7765	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7075	Discontinued
0.7719	Intermediate Similarity	NPD3749	Approved
0.7706	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6559	Discontinued
0.7669	Intermediate Similarity	NPD8166	Discontinued
0.7661	Intermediate Similarity	NPD7768	Phase 2
0.7657	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7411	Suspended
0.7624	Intermediate Similarity	NPD6785	Approved
0.7624	Intermediate Similarity	NPD6784	Approved
0.7609	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8455	Phase 2
0.753	Intermediate Similarity	NPD6799	Approved
0.7529	Intermediate Similarity	NPD5494	Approved
0.7515	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7199	Phase 2
0.7486	Intermediate Similarity	NPD6959	Discontinued
0.7485	Intermediate Similarity	NPD6801	Discontinued
0.7475	Intermediate Similarity	NPD8404	Phase 2
0.7471	Intermediate Similarity	NPD919	Approved
0.7471	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD6166	Phase 2
0.7458	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3750	Approved
0.7455	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD3817	Phase 2
0.7396	Intermediate Similarity	NPD920	Approved
0.7396	Intermediate Similarity	NPD7497	Discontinued
0.7391	Intermediate Similarity	NPD6355	Discontinued
0.7384	Intermediate Similarity	NPD1934	Approved
0.7381	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4380	Phase 2
0.7365	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7236	Approved
0.7362	Intermediate Similarity	NPD3748	Approved
0.7356	Intermediate Similarity	NPD3882	Suspended
0.7345	Intermediate Similarity	NPD6232	Discontinued
0.7333	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD6100	Approved
0.7317	Intermediate Similarity	NPD6099	Approved
0.7317	Intermediate Similarity	NPD2796	Approved
0.7314	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD3764	Approved
0.7312	Intermediate Similarity	NPD6798	Discontinued
0.7312	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3226	Approved
0.7297	Intermediate Similarity	NPD8150	Discontinued
0.7294	Intermediate Similarity	NPD5403	Approved
0.7293	Intermediate Similarity	NPD7074	Phase 3
0.7283	Intermediate Similarity	NPD37	Approved
0.7278	Intermediate Similarity	NPD3818	Discontinued
0.7278	Intermediate Similarity	NPD7228	Approved
0.7278	Intermediate Similarity	NPD7177	Discontinued
0.7278	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5401	Approved
0.7273	Intermediate Similarity	NPD6234	Discontinued
0.7267	Intermediate Similarity	NPD8032	Phase 2
0.7257	Intermediate Similarity	NPD4965	Approved
0.7257	Intermediate Similarity	NPD4967	Phase 2
0.7257	Intermediate Similarity	NPD4966	Approved
0.7256	Intermediate Similarity	NPD2799	Discontinued
0.725	Intermediate Similarity	NPD7095	Approved
0.7247	Intermediate Similarity	NPD3787	Discontinued
0.7247	Intermediate Similarity	NPD7229	Phase 3
0.7244	Intermediate Similarity	NPD1608	Approved
0.7238	Intermediate Similarity	NPD7054	Approved
0.7229	Intermediate Similarity	NPD1549	Phase 2
0.7213	Intermediate Similarity	NPD7685	Pre-registration
0.7212	Intermediate Similarity	NPD1551	Phase 2
0.72	Intermediate Similarity	NPD5402	Approved
0.7198	Intermediate Similarity	NPD7472	Approved
0.7195	Intermediate Similarity	NPD7097	Phase 1
0.7186	Intermediate Similarity	NPD1243	Approved
0.7182	Intermediate Similarity	NPD7799	Discontinued
0.7182	Intermediate Similarity	NPD3751	Discontinued
0.7176	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7808	Phase 3
0.7169	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2344	Approved
0.7169	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2346	Discontinued
0.7169	Intermediate Similarity	NPD1471	Phase 3
0.716	Intermediate Similarity	NPD6233	Phase 2
0.7152	Intermediate Similarity	NPD7033	Discontinued
0.7151	Intermediate Similarity	NPD7239	Suspended
0.7143	Intermediate Similarity	NPD4110	Phase 3
0.7143	Intermediate Similarity	NPD1465	Phase 2
0.7143	Intermediate Similarity	NPD2801	Approved
0.7143	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7435	Discontinued
0.7121	Intermediate Similarity	NPD8151	Discontinued
0.712	Intermediate Similarity	NPD7251	Discontinued
0.712	Intermediate Similarity	NPD7240	Approved
0.7111	Intermediate Similarity	NPD3926	Phase 2
0.7102	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3268	Approved
0.7095	Intermediate Similarity	NPD1247	Approved
0.7092	Intermediate Similarity	NPD7870	Phase 2
0.7092	Intermediate Similarity	NPD7871	Phase 2
0.7076	Intermediate Similarity	NPD2534	Approved
0.7076	Intermediate Similarity	NPD2533	Approved
0.7076	Intermediate Similarity	NPD2532	Approved
0.7066	Intermediate Similarity	NPD5762	Approved
0.7066	Intermediate Similarity	NPD5763	Approved
0.7065	Intermediate Similarity	NPD6797	Phase 2
0.7051	Intermediate Similarity	NPD17	Approved
0.7048	Intermediate Similarity	NPD4308	Phase 3
0.7048	Intermediate Similarity	NPD1510	Phase 2
0.7025	Intermediate Similarity	NPD3972	Approved
0.7024	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1511	Approved
0.7012	Intermediate Similarity	NPD4140	Approved
0.7005	Intermediate Similarity	NPD8407	Phase 2
0.7	Intermediate Similarity	NPD7874	Approved
0.7	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD3887	Approved
0.7	Intermediate Similarity	NPD2797	Approved
0.7	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2354	Approved
0.7	Intermediate Similarity	NPD2309	Approved
0.6995	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8485	Approved
0.6994	Remote Similarity	NPD2313	Discontinued
0.6989	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6832	Phase 2
0.6974	Remote Similarity	NPD6778	Approved
0.6974	Remote Similarity	NPD6776	Approved
0.6974	Remote Similarity	NPD6779	Approved
0.6974	Remote Similarity	NPD6782	Approved
0.6974	Remote Similarity	NPD6780	Approved
0.6974	Remote Similarity	NPD4107	Approved
0.6974	Remote Similarity	NPD6781	Approved
0.6974	Remote Similarity	NPD6777	Approved
0.6971	Remote Similarity	NPD7028	Phase 2
0.6954	Remote Similarity	NPD7696	Phase 3
0.6954	Remote Similarity	NPD7698	Approved
0.6954	Remote Similarity	NPD7697	Approved
0.6947	Remote Similarity	NPD8435	Approved
0.6947	Remote Similarity	NPD8361	Approved
0.6947	Remote Similarity	NPD8360	Approved
0.6936	Remote Similarity	NPD1512	Approved
0.6936	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD8368	Discontinued
0.6933	Remote Similarity	NPD7008	Discontinued
0.6932	Remote Similarity	NPD6677	Suspended
0.6931	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1607	Approved
0.6923	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD8320	Phase 1
0.6919	Remote Similarity	NPD8319	Approved
0.6909	Remote Similarity	NPD1240	Approved
0.6909	Remote Similarity	NPD4307	Phase 2
0.6909	Remote Similarity	NPD4060	Phase 1
0.6905	Remote Similarity	NPD2438	Suspended
0.6905	Remote Similarity	NPD2935	Discontinued
0.6904	Remote Similarity	NPD3057	Approved
0.69	Remote Similarity	NPD7701	Phase 2
0.6894	Remote Similarity	NPD3267	Approved
0.6894	Remote Similarity	NPD3266	Approved
0.6893	Remote Similarity	NPD7577	Discontinued
0.689	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2800	Approved
0.6881	Remote Similarity	NPD7801	Approved
0.6881	Remote Similarity	NPD7783	Phase 2
0.6881	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4908	Phase 1

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