NPASS Compound

Structure

NPC12326 OpenBabel07101718192D 52 59 0 0 1 0 0 0 0 0999 V2000 8.3664 -5.7964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3664 -4.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5297 -6.2794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5297 -4.3473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6931 -5.7964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8565 -4.3473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6733 -4.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1248 0.5849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6733 -5.7964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0772 0.7470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8565 -3.3812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3465 -4.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4056 -1.0646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8321 -1.3292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1055 -0.2635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3465 -1.9321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6733 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6931 -4.8303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5099 -4.3473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7890 -0.3209 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7764 -0.5866 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5099 -1.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5099 -6.2794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6937 0.0033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5099 -0.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3465 -5.7964 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3579 -0.9025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2168 -1.7487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4902 -0.6830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8366 -0.4830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3465 -2.8982 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0198 -2.8982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5459 -1.4256 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8366 -1.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5099 -3.3812 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6733 -1.9321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8366 -1.4491 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8366 -0.4830 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3729 0.5018 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5099 -7.2455 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6461 0.1654 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3465 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1832 -6.2794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9745 -1.6463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3612 -3.6755 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0198 -1.9321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6733 -1.9321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1832 -3.3812 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6733 -2.8982 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1250 -0.2635 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 18 2 0 0 0 0 5 18 1 0 0 0 0 6 11 2 0 0 0 0 6 18 1 0 0 0 0 7 9 2 0 0 0 0 7 19 1 0 0 0 0 8 10 2 0 0 0 0 8 20 1 0 0 0 0 9 23 1 0 0 0 0 10 24 1 0 0 0 0 11 32 1 0 0 0 0 12 19 2 0 0 0 0 12 26 1 0 0 0 0 13 20 2 0 0 0 0 13 27 1 0 0 0 0 14 21 2 0 0 0 0 14 28 1 0 0 0 0 15 21 1 0 0 0 0 15 29 2 0 0 0 0 16 22 1 0 0 0 0 16 31 1 0 0 0 0 17 25 2 0 0 0 0 17 30 1 0 0 0 0 21 40 1 0 0 0 0 22 25 1 0 0 0 0 22 37 2 0 0 0 0 23 26 2 0 0 0 0 23 41 1 0 0 0 0 24 27 2 0 0 0 0 24 42 1 0 0 0 0 25 43 1 0 0 0 0 26 44 1 0 0 0 0 27 45 1 0 0 0 0 28 33 2 0 0 0 0 28 46 1 0 0 0 0 29 33 1 0 0 0 0 29 51 1 0 0 0 0 30 34 2 0 0 0 0 30 52 1 0 0 0 0 31 36 1 0 0 0 0 31 49 1 1 0 0 0 32 47 2 0 0 0 0 32 49 1 0 0 0 0 34 35 1 0 0 0 0 34 37 1 0 0 0 0 35 33 1 1 0 0 0 35 38 1 0 0 0 0 36 19 1 1 0 0 0 36 50 1 0 0 0 0 37 50 1 0 0 0 0 38 39 1 1 0 0 0 38 48 1 0 0 0 0 39 20 1 1 0 0 0 39 51 1 0 0 0 0 39 52 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	706.17
Volume:	684.101
LogP:	4.898
LogD:	2.955
LogS:	-3.613
# Rotatable Bonds:	6
TPSA:	215.83
# H-Bond Aceptor:	13
# H-Bond Donor:	8
# Rings:	8
# Heavy Atoms:	13

MedChem Properties

QED Drug-Likeness Score:	0.068
Synthetic Accessibility Score:	5.497
Fsp3:	0.154
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.39
MDCK Permeability:	6.9272964537958615e-06
Pgp-inhibitor:	0.098
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.651
20% Bioavailability (F20%):	0.905
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	96.80005645751953%
Volume Distribution (VD):	0.225
Pgp-substrate:	2.142582893371582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.173
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.9
CYP2C9-substrate:	0.987
CYP2D6-inhibitor:	0.108
CYP2D6-substrate:	0.175
CYP3A4-inhibitor:	0.199
CYP3A4-substrate:	0.262

ADMET: Excretion

Clearance (CL):	7.373
Half-life (T1/2):	0.586

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.189
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.38
Rat Oral Acute Toxicity:	0.899
Maximum Recommended Daily Dose:	0.825
Skin Sensitization:	0.951
Carcinogencity:	0.592
Eye Corrosion:	0.003
Eye Irritation:	0.919
Respiratory Toxicity:	0.03

Download Data

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

Natural Product: NPC12326

Natural Product ID:	NPC12326
*Common Name:**	CUSOOPMZIJVVAK-FDHSEBRCSA-N
IUPAC Name:	n.a.
Synonyms:	3'-O-cinnamoylprocyanidin A-2
Standard InCHIKey:	CUSOOPMZIJVVAK-FDHSEBRCSA-N
Standard InCHI:	InChI=1S/C39H30O13/c40-21-14-28(46)33-29(15-21)51-39(20-8-10-24(42)27(45)13-20)38(48)35(33)34-30(52-39)17-25(43)22-16-31(49-32(47)11-6-18-4-2-1-3-5-18)36(50-37(22)34)19-7-9-23(41)26(44)12-19/h1-15,17,31,35-36,38,40-46,48H,16H2/b11-6+/t31-,35-,36-,38-,39+/m1/s1
SMILES:	O=C(O[C@@H]1Cc2c(O)cc3c(c2O[C@@H]1c1ccc(c(c1)O)O)[C@H]1c2c(O)cc(cc2O[C@@](O3)([C@@H]1O)c1ccc(c(c1)O)O)O)/C=C/c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508297
PubChem CID:	21593936
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO21558	Ormosia sumatrana	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15568789]
NPO21558	Ormosia sumatrana	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
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Inhibition	<	10.0	%	PMID[537049]

☑ 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 NPC12326 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	396
0.1-0.2	1676
0.2-0.3	4011
0.3-0.4	9710
0.4-0.5	8650
0.5-0.6	4035
0.6-0.7	6098
0.7-0.8	6918
0.8-0.85	994
0.85-0.9	149
0.9-0.95	57
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC134911
0.9412	High Similarity	NPC272552
0.9412	High Similarity	NPC322899
0.9412	High Similarity	NPC44192
0.9412	High Similarity	NPC226108
0.9412	High Similarity	NPC46283
0.9412	High Similarity	NPC469944
0.9359	High Similarity	NPC147743
0.9359	High Similarity	NPC4809
0.9359	High Similarity	NPC73517
0.9299	High Similarity	NPC159526
0.9299	High Similarity	NPC212614
0.9299	High Similarity	NPC151474
0.9299	High Similarity	NPC86630
0.9299	High Similarity	NPC471404
0.9299	High Similarity	NPC205613
0.9299	High Similarity	NPC106601
0.9226	High Similarity	NPC20050
0.9226	High Similarity	NPC306267
0.9177	High Similarity	NPC185231
0.9161	High Similarity	NPC226809
0.9161	High Similarity	NPC279406
0.9114	High Similarity	NPC125495
0.9103	High Similarity	NPC224161
0.9085	High Similarity	NPC263940
0.9085	High Similarity	NPC204770
0.9085	High Similarity	NPC236202
0.9085	High Similarity	NPC108811
0.9085	High Similarity	NPC170103
0.9085	High Similarity	NPC82917
0.9085	High Similarity	NPC58190
0.9085	High Similarity	NPC202742
0.9085	High Similarity	NPC18185
0.9085	High Similarity	NPC262911
0.9085	High Similarity	NPC294558
0.9085	High Similarity	NPC70409
0.9074	High Similarity	NPC9309
0.9045	High Similarity	NPC46335
0.9045	High Similarity	NPC8712
0.902	High Similarity	NPC155564
0.902	High Similarity	NPC102280
0.902	High Similarity	NPC248053
0.902	High Similarity	NPC96576
0.902	High Similarity	NPC268515
0.902	High Similarity	NPC40222
0.8974	High Similarity	NPC471403
0.897	High Similarity	NPC65333
0.8968	High Similarity	NPC211561
0.8957	High Similarity	NPC59516
0.8938	High Similarity	NPC478269
0.8924	High Similarity	NPC268484
0.8916	High Similarity	NPC98583
0.891	High Similarity	NPC477612
0.8903	High Similarity	NPC227516
0.8903	High Similarity	NPC20757
0.8875	High Similarity	NPC470827
0.8861	High Similarity	NPC223720
0.8861	High Similarity	NPC115203
0.8855	High Similarity	NPC100251
0.8854	High Similarity	NPC259707
0.8846	High Similarity	NPC475250
0.8834	High Similarity	NPC121290
0.8827	High Similarity	NPC478267
0.882	High Similarity	NPC166456
0.882	High Similarity	NPC98083
0.882	High Similarity	NPC470828
0.882	High Similarity	NPC7543
0.882	High Similarity	NPC24339
0.882	High Similarity	NPC94220
0.8797	High Similarity	NPC53587
0.8797	High Similarity	NPC59692
0.8797	High Similarity	NPC169404
0.8797	High Similarity	NPC176186
0.8766	High Similarity	NPC28440
0.8766	High Similarity	NPC171932
0.8765	High Similarity	NPC100936
0.8765	High Similarity	NPC1253
0.8742	High Similarity	NPC150442
0.8718	High Similarity	NPC15538
0.8718	High Similarity	NPC473480
0.8713	High Similarity	NPC321916
0.8712	High Similarity	NPC149873
0.8712	High Similarity	NPC124747
0.8712	High Similarity	NPC155754
0.8712	High Similarity	NPC7191
0.8712	High Similarity	NPC109061
0.8696	High Similarity	NPC165483
0.8693	High Similarity	NPC178054
0.8693	High Similarity	NPC277331
0.8693	High Similarity	NPC100482
0.8679	High Similarity	NPC120774
0.8679	High Similarity	NPC215060
0.8679	High Similarity	NPC264875
0.8679	High Similarity	NPC163598
0.8679	High Similarity	NPC476352
0.8675	High Similarity	NPC473818
0.8663	High Similarity	NPC318119
0.8662	High Similarity	NPC476348
0.8662	High Similarity	NPC280945
0.8662	High Similarity	NPC187398
0.8645	High Similarity	NPC76176
0.8645	High Similarity	NPC138227
0.8645	High Similarity	NPC168579
0.8645	High Similarity	NPC475492
0.8645	High Similarity	NPC469313
0.8645	High Similarity	NPC292443
0.8625	High Similarity	NPC470769
0.8621	High Similarity	NPC269046
0.8616	High Similarity	NPC473621
0.8608	High Similarity	NPC106138
0.8605	High Similarity	NPC123259
0.8605	High Similarity	NPC129533
0.8605	High Similarity	NPC132111
0.8599	High Similarity	NPC476347
0.8598	High Similarity	NPC177100
0.8598	High Similarity	NPC139540
0.859	High Similarity	NPC143120
0.859	High Similarity	NPC473909
0.859	High Similarity	NPC274960
0.8589	High Similarity	NPC173726
0.8589	High Similarity	NPC241600
0.8588	High Similarity	NPC79736
0.8588	High Similarity	NPC67629
0.8581	High Similarity	NPC37793
0.858	High Similarity	NPC11411
0.8571	High Similarity	NPC157333
0.8571	High Similarity	NPC180768
0.8563	High Similarity	NPC237202
0.8562	High Similarity	NPC478268
0.8562	High Similarity	NPC233467
0.8562	High Similarity	NPC302610
0.8553	High Similarity	NPC120426
0.8553	High Similarity	NPC476871
0.8553	High Similarity	NPC294522
0.8553	High Similarity	NPC21184
0.8553	High Similarity	NPC205727
0.8547	High Similarity	NPC208797
0.8547	High Similarity	NPC125352
0.8547	High Similarity	NPC8940
0.8547	High Similarity	NPC53680
0.8544	High Similarity	NPC102934
0.8544	High Similarity	NPC281549
0.8544	High Similarity	NPC252402
0.8544	High Similarity	NPC93924
0.8538	High Similarity	NPC267549
0.8535	High Similarity	NPC199928
0.8535	High Similarity	NPC125755
0.8526	High Similarity	NPC232228
0.8523	High Similarity	NPC264302
0.8521	High Similarity	NPC47140
0.8521	High Similarity	NPC67134
0.8509	High Similarity	NPC474656
0.8509	High Similarity	NPC475141
0.8506	High Similarity	NPC262189
0.8491	Intermediate Similarity	NPC94871
0.8491	Intermediate Similarity	NPC306890
0.8491	Intermediate Similarity	NPC476398
0.8491	Intermediate Similarity	NPC30688
0.8491	Intermediate Similarity	NPC259347
0.8491	Intermediate Similarity	NPC471062
0.8491	Intermediate Similarity	NPC321657
0.8491	Intermediate Similarity	NPC318373
0.8491	Intermediate Similarity	NPC176903
0.8491	Intermediate Similarity	NPC470933
0.8491	Intermediate Similarity	NPC476386
0.8491	Intermediate Similarity	NPC473427
0.8488	Intermediate Similarity	NPC80956
0.8485	Intermediate Similarity	NPC216916
0.8481	Intermediate Similarity	NPC232992
0.8481	Intermediate Similarity	NPC52740
0.8481	Intermediate Similarity	NPC41844
0.8476	Intermediate Similarity	NPC230531
0.8476	Intermediate Similarity	NPC215400
0.8471	Intermediate Similarity	NPC277867
0.8471	Intermediate Similarity	NPC161700
0.8471	Intermediate Similarity	NPC469701
0.8471	Intermediate Similarity	NPC163898
0.8466	Intermediate Similarity	NPC228357
0.8457	Intermediate Similarity	NPC473736
0.8457	Intermediate Similarity	NPC179947
0.8457	Intermediate Similarity	NPC65489
0.8452	Intermediate Similarity	NPC186406
0.8448	Intermediate Similarity	NPC231254
0.8447	Intermediate Similarity	NPC472612
0.8447	Intermediate Similarity	NPC289967
0.8447	Intermediate Similarity	NPC21902
0.8447	Intermediate Similarity	NPC472611
0.8438	Intermediate Similarity	NPC257970
0.8438	Intermediate Similarity	NPC205501
0.8438	Intermediate Similarity	NPC472710
0.8438	Intermediate Similarity	NPC472709
0.8438	Intermediate Similarity	NPC162976
0.8438	Intermediate Similarity	NPC470927
0.8438	Intermediate Similarity	NPC118000
0.8434	Intermediate Similarity	NPC476372
0.8434	Intermediate Similarity	NPC476371
0.8428	Intermediate Similarity	NPC473408
0.8428	Intermediate Similarity	NPC478237
0.8427	Intermediate Similarity	NPC477082
0.8424	Intermediate Similarity	NPC24164

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 NPC12326 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	952
0.2-0.3	1864
0.3-0.4	2729
0.4-0.5	1713
0.5-0.6	932
0.6-0.7	503
0.7-0.8	108
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8412	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD1653	Approved
0.8354	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD8455	Phase 2
0.817	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD1613	Approved
0.8161	Intermediate Similarity	NPD8313	Approved
0.8161	Intermediate Similarity	NPD8312	Approved
0.814	Intermediate Similarity	NPD7074	Phase 3
0.8129	Intermediate Similarity	NPD7228	Approved
0.8089	Intermediate Similarity	NPD7266	Discontinued
0.8012	Intermediate Similarity	NPD6166	Phase 2
0.8012	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD7054	Approved
0.7977	Intermediate Similarity	NPD5844	Phase 1
0.7931	Intermediate Similarity	NPD7472	Approved
0.7929	Intermediate Similarity	NPD6234	Discontinued
0.7922	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7886	Intermediate Similarity	NPD6797	Phase 2
0.7844	Intermediate Similarity	NPD37	Approved
0.7843	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7251	Discontinued
0.7836	Intermediate Similarity	NPD7199	Phase 2
0.7833	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD3818	Discontinued
0.7811	Intermediate Similarity	NPD4966	Approved
0.7811	Intermediate Similarity	NPD4965	Approved
0.7811	Intermediate Similarity	NPD4967	Phase 2
0.7798	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD7808	Phase 3
0.7792	Intermediate Similarity	NPD4908	Phase 1
0.7771	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3027	Phase 3
0.774	Intermediate Similarity	NPD6559	Discontinued
0.7706	Intermediate Similarity	NPD7768	Phase 2
0.7701	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1465	Phase 2
0.7667	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD5124	Phase 1
0.7658	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6674	Discontinued
0.7644	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7240	Approved
0.7633	Intermediate Similarity	NPD1934	Approved
0.763	Intermediate Similarity	NPD6959	Discontinued
0.7619	Intermediate Similarity	NPD4380	Phase 2
0.7598	Intermediate Similarity	NPD7549	Discontinued
0.7558	Intermediate Similarity	NPD7075	Discontinued
0.7544	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6232	Discontinued
0.7485	Intermediate Similarity	NPD7819	Suspended
0.7484	Intermediate Similarity	NPD4060	Phase 1
0.7471	Intermediate Similarity	NPD7411	Suspended
0.7471	Intermediate Similarity	NPD5494	Approved
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7473	Discontinued
0.7453	Intermediate Similarity	NPD7097	Phase 1
0.7451	Intermediate Similarity	NPD1610	Phase 2
0.7435	Intermediate Similarity	NPD7680	Approved
0.7429	Intermediate Similarity	NPD8127	Discontinued
0.7423	Intermediate Similarity	NPD8151	Discontinued
0.7416	Intermediate Similarity	NPD3751	Discontinued
0.7386	Intermediate Similarity	NPD3787	Discontinued
0.7384	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD6190	Approved
0.7348	Intermediate Similarity	NPD7685	Pre-registration
0.7341	Intermediate Similarity	NPD3817	Phase 2
0.7341	Intermediate Similarity	NPD5402	Approved
0.7337	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD1652	Phase 2
0.7326	Intermediate Similarity	NPD6801	Discontinued
0.7321	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7316	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3750	Approved
0.7289	Intermediate Similarity	NPD8166	Discontinued
0.7289	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2801	Approved
0.7278	Intermediate Similarity	NPD2861	Phase 2
0.7262	Intermediate Similarity	NPD1511	Approved
0.7262	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.7235	Intermediate Similarity	NPD5403	Approved
0.7226	Intermediate Similarity	NPD1091	Approved
0.72	Intermediate Similarity	NPD3882	Suspended
0.7188	Intermediate Similarity	NPD4625	Phase 3
0.7176	Intermediate Similarity	NPD1512	Approved
0.7172	Intermediate Similarity	NPD7783	Phase 2
0.7172	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8054	Approved
0.7135	Intermediate Similarity	NPD8053	Approved
0.7126	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD5401	Approved
0.7118	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD422	Phase 1
0.7083	Intermediate Similarity	NPD4628	Phase 3
0.7078	Intermediate Similarity	NPD1548	Phase 1
0.7069	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD1549	Phase 2
0.7062	Intermediate Similarity	NPD3749	Approved
0.7037	Intermediate Similarity	NPD6798	Discontinued
0.7037	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4749	Approved
0.7018	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5763	Approved
0.7006	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD7229	Phase 3
0.7	Intermediate Similarity	NPD5058	Phase 3
0.699	Remote Similarity	NPD7435	Discontinued
0.6988	Remote Similarity	NPD3748	Approved
0.6982	Remote Similarity	NPD7003	Approved
0.6966	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7213	Phase 3
0.6959	Remote Similarity	NPD6799	Approved
0.6959	Remote Similarity	NPD7212	Phase 2
0.6954	Remote Similarity	NPD7871	Phase 2
0.6954	Remote Similarity	NPD8319	Approved
0.6954	Remote Similarity	NPD8320	Phase 1
0.6954	Remote Similarity	NPD7870	Phase 2
0.6952	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD2935	Discontinued
0.6931	Remote Similarity	NPD6841	Approved
0.6931	Remote Similarity	NPD6843	Phase 3
0.6931	Remote Similarity	NPD6842	Approved
0.6923	Remote Similarity	NPD6779	Approved
0.6923	Remote Similarity	NPD6776	Approved
0.6923	Remote Similarity	NPD6781	Approved
0.6923	Remote Similarity	NPD6778	Approved
0.6923	Remote Similarity	NPD6780	Approved
0.6923	Remote Similarity	NPD6782	Approved
0.6923	Remote Similarity	NPD6777	Approved
0.6919	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7447	Phase 1
0.6918	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6599	Discontinued
0.6909	Remote Similarity	NPD230	Phase 1
0.6909	Remote Similarity	NPD6355	Discontinued
0.6904	Remote Similarity	NPD7697	Approved
0.6904	Remote Similarity	NPD7696	Phase 3
0.6904	Remote Similarity	NPD7698	Approved
0.689	Remote Similarity	NPD6233	Phase 2
0.6879	Remote Similarity	NPD6273	Approved
0.6879	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD8150	Discontinued
0.6875	Remote Similarity	NPD8651	Approved
0.6871	Remote Similarity	NPD7095	Approved
0.6866	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6866	Remote Similarity	NPD7874	Approved
0.6864	Remote Similarity	NPD2424	Discontinued
0.6857	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6823	Phase 2
0.6852	Remote Similarity	NPD3018	Phase 2
0.685	Remote Similarity	NPD7701	Phase 2
0.6848	Remote Similarity	NPD4140	Approved
0.6848	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3620	Phase 2
0.6845	Remote Similarity	NPD1551	Phase 2
0.6832	Remote Similarity	NPD2797	Approved
0.6826	Remote Similarity	NPD4536	Approved
0.6826	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD4538	Approved
0.6821	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6811	Remote Similarity	NPD8156	Discontinued
0.6807	Remote Similarity	NPD4340	Discontinued
0.6807	Remote Similarity	NPD1933	Approved
0.6786	Remote Similarity	NPD1510	Phase 2
0.6786	Remote Similarity	NPD5588	Approved
0.6786	Remote Similarity	NPD5960	Phase 3
0.6784	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4626	Approved
0.677	Remote Similarity	NPD3225	Approved
0.6766	Remote Similarity	NPD7585	Approved
0.6765	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7390	Discontinued
0.6761	Remote Similarity	NPD3226	Approved
0.6757	Remote Similarity	NPD8099	Discontinued
0.6757	Remote Similarity	NPD8252	Approved
0.6757	Remote Similarity	NPD8251	Approved
0.6749	Remote Similarity	NPD7801	Approved
0.6746	Remote Similarity	NPD6100	Approved
0.6746	Remote Similarity	NPD6099	Approved
0.6746	Remote Similarity	NPD5404	Approved
0.6746	Remote Similarity	NPD5405	Approved
0.6746	Remote Similarity	NPD5408	Approved
0.6746	Remote Similarity	NPD5406	Approved
0.6746	Remote Similarity	NPD2796	Approved
0.674	Remote Similarity	NPD919	Approved
0.6735	Remote Similarity	NPD7699	Phase 2
0.6735	Remote Similarity	NPD7700	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