NPASS Compound

Structure

NPC16912 OpenBabel07101718242D 46 49 0 0 1 0 0 0 0 0999 V2000 -1.7211 -3.1370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0362 2.4510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5222 -3.3196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3022 2.5467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6986 -0.1941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2550 -1.3938 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3552 -0.4403 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3786 0.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4438 1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6135 1.5327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4438 0.0946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7832 1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6135 -0.3847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2903 0.9433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8758 -0.7454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7731 -3.2799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1200 2.7336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2718 -2.7218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0050 1.8945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6986 -1.1528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7832 0.0946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6305 1.1468 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1622 -1.5428 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3439 -1.0732 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1245 0.6772 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0380 -1.1528 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2923 -0.3847 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9529 -0.3847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4794 -0.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4439 0.2702 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2781 0.0042 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9378 -0.1993 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4228 -4.1724 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9067 3.6684 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1642 -3.0721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9212 2.1771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5289 -1.6322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9529 -1.3435 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0960 -0.4326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1753 -2.5304 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4172 2.0815 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1289 -1.7737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7917 0.9598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8683 -1.6322 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1226 0.0946 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 17 1 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 29 1 0 0 0 0 7 29 1 0 0 0 0 8 30 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 2 0 0 0 0 12 21 2 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 14 30 1 0 0 0 0 15 31 1 0 0 0 0 15 40 1 0 0 0 0 16 33 2 0 0 0 0 16 40 1 0 0 0 0 17 34 2 0 0 0 0 17 41 1 0 0 0 0 18 35 2 0 0 0 0 18 42 1 0 0 0 0 19 36 2 0 0 0 0 19 43 1 0 0 0 0 20 37 2 0 0 0 0 20 44 1 0 0 0 0 21 28 1 0 0 0 0 22 25 1 0 0 0 0 22 41 1 6 0 0 0 23 24 1 0 0 0 0 23 26 1 0 0 0 0 23 29 1 1 0 0 0 24 27 1 0 0 0 0 24 42 1 1 0 0 0 25 31 1 6 0 0 0 25 43 1 0 0 0 0 26 32 1 1 0 0 0 26 44 1 0 0 0 0 27 31 1 1 0 0 0 27 45 1 0 0 0 0 28 38 2 0 0 0 0 28 45 1 0 0 0 0 29 46 1 0 0 0 0 30 32 1 6 0 0 0 30 39 1 0 0 0 0 31 32 1 1 0 0 0 32 46 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	648.24
Volume:	627.137
LogP:	2.629
LogD:	1.455
LogS:	-4.224
# Rotatable Bonds:	14
TPSA:	187.26
# H-Bond Aceptor:	14
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.318
Synthetic Accessibility Score:	6.033
Fsp3:	0.625
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:	-5.369
MDCK Permeability:	0.00011820987856481224
Pgp-inhibitor:	0.999
Pgp-substrate:	0.061
Human Intestinal Absorption (HIA):	0.857
20% Bioavailability (F20%):	0.985
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.376
Plasma Protein Binding (PPB):	26.15121078491211%
Volume Distribution (VD):	1.526
Pgp-substrate:	38.25543212890625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.029
CYP1A2-substrate:	0.017
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.006
CYP2D6-inhibitor:	0.944
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.316
CYP3A4-substrate:	0.446

ADMET: Excretion

Clearance (CL):	2.843
Half-life (T1/2):	0.785

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.918
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.111
Maximum Recommended Daily Dose:	0.024
Skin Sensitization:	0.285
Carcinogencity:	0.183
Eye Corrosion:	0.004
Eye Irritation:	0.055
Respiratory Toxicity:	0.092

Download Data

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

Natural Product: NPC16912

Natural Product ID:	NPC16912
*Common Name:**	SIEZSHWOPJNWFA-SQSDACCSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	SIEZSHWOPJNWFA-SQSDACCSSA-N
Standard InCHI:	InChI=1S/C32H40O14/c1-16(33)40-15-31-25(43-19(4)36)22(41-17(2)34)14-30(8,39)32(31)26(44-20(5)37)23(29(6,7)46-32)24(42-18(3)35)27(31)45-28(38)21-12-10-9-11-13-21/h9-13,22-27,39H,14-15H2,1-8H3/t22-,23+,24-,25-,26+,27-,30-,31-,32-/m0/s1
SMILES:	CC(=O)OC[C@]12[C@H]([C@H](C[C@@](C)([C@]32[C@@H]([C@@H]([C@@H]([C@@H]1OC(=O)c1ccccc1)OC(=O)C)C(C)(C)O3)OC(=O)C)O)OC(=O)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3577221
PubChem CID:	14078468
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002967] Hexacarboxylic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18616221]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	stems	Montecristo National Park, province of Santa Ana, El Salvador	2004-JUN	PMID[20873773]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21419633]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25695368]
NPO15653	Celastrus vulcanicola	Species	Celastraceae	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
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Activity	=	69.9	%	PMID[566964]

☑ 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 NPC16912 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	279
0.1-0.2	1047
0.2-0.3	2164
0.3-0.4	4130
0.4-0.5	8097
0.5-0.6	11891
0.6-0.7	12472
0.7-0.8	2048
0.8-0.85	259
0.85-0.9	135
0.9-0.95	84
0.95-1	91

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC171207
0.9924	High Similarity	NPC97667
0.985	High Similarity	NPC87448
0.985	High Similarity	NPC472576
0.985	High Similarity	NPC291599
0.985	High Similarity	NPC41481
0.985	High Similarity	NPC97947
0.985	High Similarity	NPC27377
0.985	High Similarity	NPC118080
0.9778	High Similarity	NPC11685
0.9778	High Similarity	NPC476974
0.9778	High Similarity	NPC472570
0.9778	High Similarity	NPC57628
0.9778	High Similarity	NPC25768
0.9778	High Similarity	NPC188865
0.9778	High Similarity	NPC472569
0.9778	High Similarity	NPC472573
0.9778	High Similarity	NPC95810
0.9778	High Similarity	NPC70716
0.9778	High Similarity	NPC95265
0.9778	High Similarity	NPC163719
0.9778	High Similarity	NPC125106
0.9774	High Similarity	NPC100913
0.9774	High Similarity	NPC90614
0.9774	High Similarity	NPC275592
0.9706	High Similarity	NPC174982
0.9706	High Similarity	NPC472568
0.9706	High Similarity	NPC158663
0.9706	High Similarity	NPC470157
0.9706	High Similarity	NPC177940
0.9706	High Similarity	NPC469349
0.9706	High Similarity	NPC476973
0.9706	High Similarity	NPC471104
0.9706	High Similarity	NPC472575
0.9706	High Similarity	NPC470159
0.9706	High Similarity	NPC70403
0.9706	High Similarity	NPC171525
0.9706	High Similarity	NPC472571
0.9706	High Similarity	NPC29704
0.9706	High Similarity	NPC472572
0.9706	High Similarity	NPC96903
0.9706	High Similarity	NPC200471
0.9706	High Similarity	NPC184817
0.9706	High Similarity	NPC473088
0.9635	High Similarity	NPC474935
0.9632	High Similarity	NPC241951
0.9632	High Similarity	NPC475122
0.9632	High Similarity	NPC475759
0.9632	High Similarity	NPC470152
0.9621	High Similarity	NPC66761
0.9621	High Similarity	NPC472577
0.9621	High Similarity	NPC17877
0.9621	High Similarity	NPC291638
0.9621	High Similarity	NPC195647
0.9565	High Similarity	NPC281717
0.9559	High Similarity	NPC163087
0.9545	High Similarity	NPC474608
0.9496	High Similarity	NPC471101
0.9496	High Similarity	NPC270590
0.9496	High Similarity	NPC301556
0.9496	High Similarity	NPC476975
0.9496	High Similarity	NPC266265
0.9496	High Similarity	NPC92293
0.9485	High Similarity	NPC34012
0.9481	High Similarity	NPC473613
0.9481	High Similarity	NPC473081
0.9481	High Similarity	NPC473109
0.9481	High Similarity	NPC211137
0.9481	High Similarity	NPC184747
0.9481	High Similarity	NPC48017
0.9481	High Similarity	NPC200592
0.9481	High Similarity	NPC43241
0.9481	High Similarity	NPC473758
0.9481	High Similarity	NPC473085
0.9481	High Similarity	NPC473060
0.9481	High Similarity	NPC473112
0.9481	High Similarity	NPC472547
0.9481	High Similarity	NPC4341
0.9481	High Similarity	NPC147880
0.9481	High Similarity	NPC476094
0.9429	High Similarity	NPC470245
0.9429	High Similarity	NPC473214
0.942	High Similarity	NPC472556
0.9412	High Similarity	NPC224491
0.9407	High Similarity	NPC210591
0.9407	High Similarity	NPC214550
0.9407	High Similarity	NPC475652
0.9403	High Similarity	NPC472545
0.9403	High Similarity	NPC472551
0.9362	High Similarity	NPC470153
0.9362	High Similarity	NPC51602
0.9357	High Similarity	NPC473215
0.9343	High Similarity	NPC472546
0.9333	High Similarity	NPC183122
0.9333	High Similarity	NPC39549
0.9333	High Similarity	NPC283375
0.9275	High Similarity	NPC191082
0.9275	High Similarity	NPC147217
0.9275	High Similarity	NPC473673
0.9275	High Similarity	NPC270498
0.9275	High Similarity	NPC246480
0.9275	High Similarity	NPC177340
0.9275	High Similarity	NPC475429
0.9275	High Similarity	NPC139067
0.9242	High Similarity	NPC147561
0.9225	High Similarity	NPC471103
0.9214	High Similarity	NPC473602
0.9214	High Similarity	NPC209592
0.9214	High Similarity	NPC240115
0.9214	High Similarity	NPC48599
0.9209	High Similarity	NPC51314
0.9209	High Similarity	NPC67777
0.9209	High Similarity	NPC38696
0.9209	High Similarity	NPC470231
0.9209	High Similarity	NPC34943
0.9167	High Similarity	NPC282239
0.9161	High Similarity	NPC472548
0.9161	High Similarity	NPC477905
0.9149	High Similarity	NPC473760
0.9143	High Similarity	NPC127857
0.9137	High Similarity	NPC477894
0.9137	High Similarity	NPC91703
0.913	High Similarity	NPC266374
0.9103	High Similarity	NPC106895
0.9078	High Similarity	NPC20255
0.9065	High Similarity	NPC192658
0.9058	High Similarity	NPC477904
0.9058	High Similarity	NPC183270
0.9041	High Similarity	NPC472393
0.9034	High Similarity	NPC473611
0.9034	High Similarity	NPC34066
0.9034	High Similarity	NPC472549
0.9034	High Similarity	NPC473670
0.9034	High Similarity	NPC21410
0.9021	High Similarity	NPC31829
0.9021	High Similarity	NPC112216
0.9021	High Similarity	NPC469448
0.9021	High Similarity	NPC7095
0.9014	High Similarity	NPC217918
0.9007	High Similarity	NPC471107
0.9007	High Similarity	NPC311825
0.9007	High Similarity	NPC125882
0.9007	High Similarity	NPC92867
0.9007	High Similarity	NPC471100
0.898	High Similarity	NPC471102
0.8978	High Similarity	NPC472374
0.8978	High Similarity	NPC472372
0.8973	High Similarity	NPC217091
0.8958	High Similarity	NPC469415
0.8951	High Similarity	NPC60509
0.8951	High Similarity	NPC81698
0.8951	High Similarity	NPC76103
0.8951	High Similarity	NPC250046
0.8944	High Similarity	NPC312393
0.8944	High Similarity	NPC478263
0.8939	High Similarity	NPC473082
0.8939	High Similarity	NPC476970
0.8929	High Similarity	NPC182869
0.8921	High Similarity	NPC87934
0.8921	High Similarity	NPC162613
0.8905	High Similarity	NPC477893
0.8905	High Similarity	NPC477896
0.8904	High Similarity	NPC469422
0.8904	High Similarity	NPC132599
0.8904	High Similarity	NPC473632
0.8904	High Similarity	NPC228204
0.8904	High Similarity	NPC469730
0.8904	High Similarity	NPC26033
0.8889	High Similarity	NPC91730
0.8889	High Similarity	NPC198455
0.8889	High Similarity	NPC476977
0.8889	High Similarity	NPC222102
0.8889	High Similarity	NPC161239
0.8889	High Similarity	NPC165260
0.8889	High Similarity	NPC303429
0.8889	High Similarity	NPC254558
0.8889	High Similarity	NPC476173
0.8881	High Similarity	NPC327031
0.8873	High Similarity	NPC478264
0.8872	High Similarity	NPC476971
0.8872	High Similarity	NPC476972
0.8864	High Similarity	NPC473083
0.8851	High Similarity	NPC469399
0.8849	High Similarity	NPC9905
0.8844	High Similarity	NPC323001
0.8844	High Similarity	NPC326235
0.8836	High Similarity	NPC249471
0.8836	High Similarity	NPC472658
0.8836	High Similarity	NPC472030
0.8836	High Similarity	NPC1173
0.8836	High Similarity	NPC304876
0.8836	High Similarity	NPC472022
0.8836	High Similarity	NPC257213
0.8836	High Similarity	NPC473414
0.8836	High Similarity	NPC469477
0.8836	High Similarity	NPC472005
0.8836	High Similarity	NPC77719
0.8836	High Similarity	NPC242262
0.8836	High Similarity	NPC265395
0.8836	High Similarity	NPC158333

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 NPC16912 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	677
0.2-0.3	1378
0.3-0.4	2690
0.4-0.5	2380
0.5-0.6	1305
0.6-0.7	449
0.7-0.8	43
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8143	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD7236	Approved
0.8012	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD7239	Suspended
0.795	Intermediate Similarity	NPD7799	Discontinued
0.7939	Intermediate Similarity	NPD8407	Phase 2
0.7866	Intermediate Similarity	NPD8368	Discontinued
0.7844	Intermediate Similarity	NPD8434	Phase 2
0.7647	Intermediate Similarity	NPD8361	Approved
0.7647	Intermediate Similarity	NPD8360	Approved
0.7647	Intermediate Similarity	NPD8435	Approved
0.7574	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD4198	Discontinued
0.7552	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD7741	Discontinued
0.7531	Intermediate Similarity	NPD8127	Discontinued
0.7529	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD7008	Discontinued
0.75	Intermediate Similarity	NPD2629	Approved
0.75	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD7058	Phase 2
0.75	Intermediate Similarity	NPD8166	Discontinued
0.75	Intermediate Similarity	NPD7057	Phase 3
0.7483	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD3764	Approved
0.7463	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD7961	Discontinued
0.7386	Intermediate Similarity	NPD8485	Approved
0.7372	Intermediate Similarity	NPD5951	Approved
0.7338	Intermediate Similarity	NPD6190	Approved
0.7326	Intermediate Similarity	NPD8150	Discontinued
0.7312	Intermediate Similarity	NPD37	Approved
0.7305	Intermediate Similarity	NPD5126	Approved
0.7305	Intermediate Similarity	NPD5125	Phase 3
0.7301	Intermediate Similarity	NPD6234	Discontinued
0.7284	Intermediate Similarity	NPD4966	Approved
0.7284	Intermediate Similarity	NPD4965	Approved
0.7284	Intermediate Similarity	NPD4967	Phase 2
0.7267	Intermediate Similarity	NPD7819	Suspended
0.7263	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5844	Phase 1
0.7261	Intermediate Similarity	NPD6273	Approved
0.719	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD2182	Approved
0.7183	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7134	Intermediate Similarity	NPD7075	Discontinued
0.7133	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7458	Discontinued
0.7115	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7228	Approved
0.7081	Intermediate Similarity	NPD6599	Discontinued
0.7067	Intermediate Similarity	NPD6663	Approved
0.7066	Intermediate Similarity	NPD6232	Discontinued
0.7063	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5760	Phase 2
0.7055	Intermediate Similarity	NPD5761	Phase 2
0.7052	Intermediate Similarity	NPD8313	Approved
0.7052	Intermediate Similarity	NPD8312	Approved
0.7051	Intermediate Similarity	NPD7003	Approved
0.7049	Intermediate Similarity	NPD7497	Discontinued
0.7045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5736	Approved
0.7019	Intermediate Similarity	NPD6591	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD2532	Approved
0.6981	Remote Similarity	NPD2533	Approved
0.6981	Remote Similarity	NPD2534	Approved
0.6981	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6858	Approved
0.6978	Remote Similarity	NPD7094	Approved
0.6975	Remote Similarity	NPD4380	Phase 2
0.6974	Remote Similarity	NPD230	Phase 1
0.6974	Remote Similarity	NPD6355	Discontinued
0.6972	Remote Similarity	NPD7610	Discontinued
0.697	Remote Similarity	NPD7768	Phase 2
0.6966	Remote Similarity	NPD6287	Discontinued
0.6957	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8455	Phase 2
0.6946	Remote Similarity	NPD5494	Approved
0.6936	Remote Similarity	NPD7240	Approved
0.6936	Remote Similarity	NPD7685	Pre-registration
0.6936	Remote Similarity	NPD6765	Approved
0.6936	Remote Similarity	NPD6764	Approved
0.6936	Remote Similarity	NPD6559	Discontinued
0.6931	Remote Similarity	NPD8462	Phase 1
0.6918	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3226	Approved
0.6914	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5402	Approved
0.6909	Remote Similarity	NPD3817	Phase 2
0.6909	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7199	Phase 2
0.6903	Remote Similarity	NPD2935	Discontinued
0.689	Remote Similarity	NPD6801	Discontinued
0.6889	Remote Similarity	NPD164	Approved
0.6875	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD7266	Discontinued
0.6859	Remote Similarity	NPD2346	Discontinued
0.6848	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6233	Phase 2
0.6842	Remote Similarity	NPD8032	Phase 2
0.6842	Remote Similarity	NPD1238	Approved
0.6835	Remote Similarity	NPD3750	Approved
0.6835	Remote Similarity	NPD4110	Phase 3
0.6835	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD7411	Suspended
0.6824	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD7095	Approved
0.6815	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD1930	Approved
0.6815	Remote Similarity	NPD1929	Approved
0.6813	Remote Similarity	NPD6799	Approved
0.6806	Remote Similarity	NPD9545	Approved
0.6802	Remote Similarity	NPD3818	Discontinued
0.6795	Remote Similarity	NPD5404	Approved
0.6795	Remote Similarity	NPD5406	Approved
0.6795	Remote Similarity	NPD2438	Suspended
0.6795	Remote Similarity	NPD5405	Approved
0.6795	Remote Similarity	NPD5408	Approved
0.679	Remote Similarity	NPD5403	Approved
0.6788	Remote Similarity	NPD8404	Phase 2
0.6788	Remote Similarity	NPD1934	Approved
0.6786	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6785	Approved
0.678	Remote Similarity	NPD6784	Approved
0.6776	Remote Similarity	NPD7699	Phase 2
0.6776	Remote Similarity	NPD6798	Discontinued
0.6776	Remote Similarity	NPD7700	Phase 2
0.6774	Remote Similarity	NPD7097	Phase 1
0.677	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.677	Remote Similarity	NPD5401	Approved
0.6763	Remote Similarity	NPD2067	Discontinued
0.6752	Remote Similarity	NPD6005	Phase 3
0.6752	Remote Similarity	NPD5763	Approved
0.6752	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6002	Phase 3
0.6752	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD6004	Phase 3
0.6752	Remote Similarity	NPD5762	Approved
0.6738	Remote Similarity	NPD8320	Phase 1
0.6738	Remote Similarity	NPD8319	Approved
0.6735	Remote Similarity	NPD4807	Approved
0.6735	Remote Similarity	NPD4806	Approved
0.6732	Remote Similarity	NPD7715	Approved
0.6732	Remote Similarity	NPD7714	Approved
0.6732	Remote Similarity	NPD7713	Phase 3
0.6731	Remote Similarity	NPD3748	Approved
0.6731	Remote Similarity	NPD2799	Discontinued
0.6726	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD2066	Phase 3
0.6716	Remote Similarity	NPD7798	Approved
0.6712	Remote Similarity	NPD5306	Approved
0.6712	Remote Similarity	NPD5305	Approved
0.6709	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6534	Approved
0.6703	Remote Similarity	NPD6535	Approved
0.6691	Remote Similarity	NPD6647	Phase 2
0.6691	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD6100	Approved
0.6688	Remote Similarity	NPD4140	Approved
0.6688	Remote Similarity	NPD6099	Approved
0.6686	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6166	Phase 2
0.6686	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD7435	Discontinued
0.6667	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3882	Suspended
0.6667	Remote Similarity	NPD7028	Phase 2
0.6667	Remote Similarity	NPD2313	Discontinued
0.6667	Remote Similarity	NPD7229	Phase 3
0.6667	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6685	Approved
0.6667	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1465	Phase 2
0.6647	Remote Similarity	NPD2801	Approved
0.6645	Remote Similarity	NPD6832	Phase 2
0.6643	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD5909	Discontinued
0.6629	Remote Similarity	NPD7074	Phase 3
0.6627	Remote Similarity	NPD3749	Approved
0.6624	Remote Similarity	NPD7305	Phase 1
0.6624	Remote Similarity	NPD4308	Phase 3
0.6608	Remote Similarity	NPD6959	Discontinued
0.66	Remote Similarity	NPD1283	Approved
0.6599	Remote Similarity	NPD3019	Approved
0.6582	Remote Similarity	NPD1551	Phase 2

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