NPASS Compound

Structure

NPC295573 OpenBabel07101719252D 46 52 0 0 1 0 0 0 0 0999 V2000 5.1470 -0.9385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6421 -5.8381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1143 0.6498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9956 -2.4084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0552 -5.8381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8513 -0.4312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4497 0.0414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3393 -4.8582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5509 1.4027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6361 -0.8801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2983 -4.3682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2983 -1.4285 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6421 -4.8582 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3047 0.0978 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1470 -2.8984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0552 -4.8582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0417 -0.9832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4497 -0.9385 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4907 -4.3682 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6241 0.4255 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1470 -3.8783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4497 -3.8783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2983 -2.4084 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -4.3682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3611 -0.6555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4497 -2.8984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -3.3883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7370 -1.0810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9038 -3.3883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4740 -2.1620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9038 -4.3682 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -1.7364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6011 -2.4084 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6421 -2.8984 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0552 -2.8984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -1.8342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0564 -0.7532 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9956 -4.3682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6011 -4.3682 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7525 -4.8582 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9810 -2.1616 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7532 -1.3052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6011 -1.4285 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4907 -3.3883 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 -0.1129 -2.1620 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 17 1 0 0 0 0 10 42 1 0 0 0 0 11 21 2 0 0 0 0 11 22 1 0 0 0 0 12 1 1 1 0 0 0 12 18 1 0 0 0 0 12 23 1 0 0 0 0 13 2 1 6 0 0 0 13 19 1 0 0 0 0 13 24 1 0 0 0 0 14 3 1 6 0 0 0 14 20 1 0 0 0 0 14 25 1 0 0 0 0 15 21 1 0 0 0 0 15 23 2 0 0 0 0 16 24 2 0 0 0 0 16 31 1 0 0 0 0 17 25 2 0 0 0 0 17 32 1 0 0 0 0 18 7 1 6 0 0 0 18 43 1 0 0 0 0 19 8 1 1 0 0 0 19 44 1 0 0 0 0 20 9 1 1 0 0 0 20 45 1 0 0 0 0 21 38 1 0 0 0 0 22 26 2 0 0 0 0 22 39 1 0 0 0 0 23 26 1 0 0 0 0 24 27 1 0 0 0 0 25 28 1 0 0 0 0 26 33 1 0 0 0 0 27 35 2 0 0 0 0 28 36 2 0 0 0 0 28 37 1 0 0 0 0 29 31 2 0 0 0 0 29 35 1 0 0 0 0 30 32 2 0 0 0 0 30 34 1 0 0 0 0 30 36 1 0 0 0 0 31 40 1 0 0 0 0 32 41 1 0 0 0 0 33 29 1 1 0 0 0 33 43 1 0 0 0 0 34 27 1 1 0 0 0 34 44 1 0 0 0 0 35 46 1 0 0 0 0 36 46 1 0 0 0 0 37 42 1 6 0 0 0 37 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	632.3
Volume:	643.997
LogP:	7.616
LogD:	3.639
LogS:	-4.62
# Rotatable Bonds:	2
TPSA:	127.07
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.223
Synthetic Accessibility Score:	5.82
Fsp3:	0.514
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:	-5.889
MDCK Permeability:	1.9504954252624884e-05
Pgp-inhibitor:	0.908
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.683
20% Bioavailability (F20%):	0.176
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	99.90422821044922%
Volume Distribution (VD):	0.59
Pgp-substrate:	3.6558010578155518%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.962
CYP2C19-inhibitor:	0.062
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.102
CYP2C9-substrate:	0.922
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.115
CYP3A4-inhibitor:	0.095
CYP3A4-substrate:	0.913

ADMET: Excretion

Clearance (CL):	2.038
Half-life (T1/2):	0.04

ADMET: Toxicity

hERG Blockers:	0.07
Human Hepatotoxicity (H-HT):	0.219
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.094
Rat Oral Acute Toxicity:	0.999
Maximum Recommended Daily Dose:	1.0
Skin Sensitization:	0.913
Carcinogencity:	0.044
Eye Corrosion:	0.003
Eye Irritation:	0.903
Respiratory Toxicity:	0.49

Download Data

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

Natural Product: NPC295573

Natural Product ID:	NPC295573
*Common Name:**	Tricitrinol A
IUPAC Name:	n.a.
Synonyms:	Tricitrinol A
Standard InCHIKey:	DYDDLIPFZTXTKD-HFFYXFNSSA-N
Standard InCHI:	InChI=1S/C37H44O9/c1-12-18(7)43-33(26-22(39)11-21(38)15(4)23(12)26)29-31(40)16(5)24-13(2)19(8)44-34-27(24)35(29)46-36-28-25(17(6)32(41)30(34)36)14(3)20(9)45-37(28)42-10/h11-14,18-20,33-34,37-41H,1-10H3/t12-,13-,14-,18-,19-,20-,33+,34-,37+/m1/s1
SMILES:	C[C@@H]1[C@@H](C)O[C@@H](c2c(cc(c(C)c12)O)O)c1c(c(C)c2[C@H](C)[C@@H](C)O[C@@H]3c2c1Oc1c2c([C@H](C)[C@@H](C)O[C@@H]2OC)c(C)c(c31)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1822981
PubChem CID:	46840959
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO33186	penicillium citrinum hgy1-5	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21761866]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	8170.0	nM	PMID[567529]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	8570.0	nM	PMID[567529]
NPT91	Cell Line	KB	Homo sapiens	IC50	>	10000.0	nM	PMID[567529]

☑ 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 NPC295573 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	443
0.1-0.2	1724
0.2-0.3	4147
0.3-0.4	10721
0.4-0.5	8065
0.5-0.6	4521
0.6-0.7	8266
0.7-0.8	4200
0.8-0.85	509
0.85-0.9	94
0.9-0.95	3
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470208
0.8936	High Similarity	NPC24913
0.8936	High Similarity	NPC177712
0.8933	High Similarity	NPC259707
0.8774	High Similarity	NPC185231
0.875	High Similarity	NPC476452
0.875	High Similarity	NPC233467
0.875	High Similarity	NPC59692
0.8741	High Similarity	NPC473107
0.869	High Similarity	NPC470308
0.869	High Similarity	NPC470307
0.8684	High Similarity	NPC471403
0.8667	High Similarity	NPC174251
0.8667	High Similarity	NPC153182
0.8652	High Similarity	NPC25729
0.8652	High Similarity	NPC474494
0.8621	High Similarity	NPC471522
0.8618	High Similarity	NPC260781
0.8618	High Similarity	NPC218041
0.8618	High Similarity	NPC469706
0.8618	High Similarity	NPC162976
0.8618	High Similarity	NPC118000
0.8618	High Similarity	NPC182368
0.8618	High Similarity	NPC145979
0.8618	High Similarity	NPC9933
0.8618	High Similarity	NPC185955
0.8618	High Similarity	NPC225815
0.8618	High Similarity	NPC469707
0.8618	High Similarity	NPC205501
0.8618	High Similarity	NPC214326
0.86	High Similarity	NPC215678
0.86	High Similarity	NPC155564
0.86	High Similarity	NPC248053
0.86	High Similarity	NPC102280
0.86	High Similarity	NPC274454
0.8591	High Similarity	NPC225445
0.859	High Similarity	NPC147743
0.859	High Similarity	NPC73517
0.859	High Similarity	NPC4809
0.8571	High Similarity	NPC200645
0.8571	High Similarity	NPC106669
0.8571	High Similarity	NPC475227
0.8562	High Similarity	NPC473621
0.8542	High Similarity	NPC469610
0.8535	High Similarity	NPC106601
0.8535	High Similarity	NPC86630
0.8535	High Similarity	NPC471404
0.8535	High Similarity	NPC159526
0.8535	High Similarity	NPC151474
0.8535	High Similarity	NPC205613
0.8535	High Similarity	NPC212614
0.8531	High Similarity	NPC8899
0.8523	High Similarity	NPC116922
0.8514	High Similarity	NPC210192
0.8506	High Similarity	NPC21902
0.8506	High Similarity	NPC226108
0.8506	High Similarity	NPC44192
0.8506	High Similarity	NPC272552
0.8506	High Similarity	NPC46283
0.8506	High Similarity	NPC322899
0.8506	High Similarity	NPC134911
0.8506	High Similarity	NPC469944
0.8483	Intermediate Similarity	NPC476615
0.8483	Intermediate Similarity	NPC476617
0.8483	Intermediate Similarity	NPC476616
0.8481	Intermediate Similarity	NPC1253
0.8481	Intermediate Similarity	NPC100936
0.8477	Intermediate Similarity	NPC14468
0.8477	Intermediate Similarity	NPC471608
0.8472	Intermediate Similarity	NPC321086
0.8472	Intermediate Similarity	NPC469611
0.8467	Intermediate Similarity	NPC177597
0.8467	Intermediate Similarity	NPC475492
0.8446	Intermediate Similarity	NPC273623
0.8425	Intermediate Similarity	NPC137580
0.8421	Intermediate Similarity	NPC111134
0.8421	Intermediate Similarity	NPC15538
0.8421	Intermediate Similarity	NPC112819
0.8421	Intermediate Similarity	NPC473480
0.8421	Intermediate Similarity	NPC133209
0.8421	Intermediate Similarity	NPC6702
0.84	Intermediate Similarity	NPC472451
0.8389	Intermediate Similarity	NPC257095
0.8389	Intermediate Similarity	NPC89686
0.8389	Intermediate Similarity	NPC273932
0.8389	Intermediate Similarity	NPC5155
0.8387	Intermediate Similarity	NPC474442
0.8387	Intermediate Similarity	NPC120633
0.8387	Intermediate Similarity	NPC473018
0.838	Intermediate Similarity	NPC473134
0.8377	Intermediate Similarity	NPC472709
0.8377	Intermediate Similarity	NPC218801
0.8377	Intermediate Similarity	NPC183380
0.8377	Intermediate Similarity	NPC472710
0.8366	Intermediate Similarity	NPC280945
0.8344	Intermediate Similarity	NPC470206
0.8344	Intermediate Similarity	NPC470207
0.8333	Intermediate Similarity	NPC49542
0.8333	Intermediate Similarity	NPC78809
0.8333	Intermediate Similarity	NPC5253
0.8333	Intermediate Similarity	NPC139976
0.8333	Intermediate Similarity	NPC20050
0.8333	Intermediate Similarity	NPC230718
0.8333	Intermediate Similarity	NPC128337
0.8333	Intermediate Similarity	NPC224161
0.8333	Intermediate Similarity	NPC84207
0.8333	Intermediate Similarity	NPC306267
0.8313	Intermediate Similarity	NPC48880
0.8312	Intermediate Similarity	NPC44452
0.8312	Intermediate Similarity	NPC107862
0.8312	Intermediate Similarity	NPC180605
0.8312	Intermediate Similarity	NPC148516
0.8312	Intermediate Similarity	NPC177172
0.8312	Intermediate Similarity	NPC321657
0.8312	Intermediate Similarity	NPC318373
0.8312	Intermediate Similarity	NPC122980
0.8311	Intermediate Similarity	NPC87777
0.8311	Intermediate Similarity	NPC472646
0.8311	Intermediate Similarity	NPC71465
0.8311	Intermediate Similarity	NPC262328
0.8311	Intermediate Similarity	NPC134260
0.8299	Intermediate Similarity	NPC11727
0.8299	Intermediate Similarity	NPC125579
0.8299	Intermediate Similarity	NPC15109
0.8299	Intermediate Similarity	NPC37410
0.8289	Intermediate Similarity	NPC161700
0.8289	Intermediate Similarity	NPC277867
0.8289	Intermediate Similarity	NPC149633
0.828	Intermediate Similarity	NPC46335
0.8278	Intermediate Similarity	NPC37793
0.8276	Intermediate Similarity	NPC473309
0.8276	Intermediate Similarity	NPC271945
0.8276	Intermediate Similarity	NPC472590
0.8276	Intermediate Similarity	NPC181497
0.8276	Intermediate Similarity	NPC160623
0.8276	Intermediate Similarity	NPC471517
0.8276	Intermediate Similarity	NPC282508
0.8269	Intermediate Similarity	NPC325860
0.8269	Intermediate Similarity	NPC279406
0.8269	Intermediate Similarity	NPC226809
0.8267	Intermediate Similarity	NPC108674
0.8267	Intermediate Similarity	NPC265075
0.8267	Intermediate Similarity	NPC100482
0.8267	Intermediate Similarity	NPC277331
0.8267	Intermediate Similarity	NPC472791
0.8267	Intermediate Similarity	NPC472792
0.8264	Intermediate Similarity	NPC96719
0.8264	Intermediate Similarity	NPC222108
0.8264	Intermediate Similarity	NPC93962
0.8258	Intermediate Similarity	NPC477612
0.8247	Intermediate Similarity	NPC179809
0.8247	Intermediate Similarity	NPC270751
0.8243	Intermediate Similarity	NPC170328
0.8243	Intermediate Similarity	NPC138350
0.8243	Intermediate Similarity	NPC197723
0.8243	Intermediate Similarity	NPC165482
0.8243	Intermediate Similarity	NPC3293
0.8243	Intermediate Similarity	NPC133463
0.8243	Intermediate Similarity	NPC472648
0.8243	Intermediate Similarity	NPC472647
0.8243	Intermediate Similarity	NPC472649
0.8243	Intermediate Similarity	NPC472800
0.8243	Intermediate Similarity	NPC191462
0.8243	Intermediate Similarity	NPC141717
0.8243	Intermediate Similarity	NPC206525
0.8243	Intermediate Similarity	NPC40664
0.8239	Intermediate Similarity	NPC293801
0.8235	Intermediate Similarity	NPC96576
0.8235	Intermediate Similarity	NPC125755
0.8224	Intermediate Similarity	NPC76176
0.8224	Intermediate Similarity	NPC473108
0.8224	Intermediate Similarity	NPC138227
0.8224	Intermediate Similarity	NPC164183
0.8224	Intermediate Similarity	NPC168579
0.8224	Intermediate Similarity	NPC473845
0.8224	Intermediate Similarity	NPC469313
0.8224	Intermediate Similarity	NPC133251
0.8219	Intermediate Similarity	NPC472798
0.8212	Intermediate Similarity	NPC472353
0.8212	Intermediate Similarity	NPC186033
0.8207	Intermediate Similarity	NPC27187
0.8207	Intermediate Similarity	NPC470225
0.8207	Intermediate Similarity	NPC254000
0.8205	Intermediate Similarity	NPC105073
0.8205	Intermediate Similarity	NPC233886
0.8205	Intermediate Similarity	NPC224528
0.8205	Intermediate Similarity	NPC157081
0.8205	Intermediate Similarity	NPC302915
0.8194	Intermediate Similarity	NPC53986
0.8194	Intermediate Similarity	NPC38664
0.8194	Intermediate Similarity	NPC215300
0.8194	Intermediate Similarity	NPC223912
0.8194	Intermediate Similarity	NPC211561
0.8182	Intermediate Similarity	NPC231712
0.8182	Intermediate Similarity	NPC262911
0.8182	Intermediate Similarity	NPC294558
0.8182	Intermediate Similarity	NPC204770
0.8182	Intermediate Similarity	NPC242774
0.8182	Intermediate Similarity	NPC237546
0.8182	Intermediate Similarity	NPC170103

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 NPC295573 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	373
0.1-0.2	998
0.2-0.3	1872
0.3-0.4	2782
0.4-0.5	1607
0.5-0.6	946
0.6-0.7	483
0.7-0.8	84
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8462	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD4908	Phase 1
0.8146	Intermediate Similarity	NPD6674	Discontinued
0.8138	Intermediate Similarity	NPD4625	Phase 3
0.7975	Intermediate Similarity	NPD6959	Discontinued
0.7959	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD7228	Approved
0.7847	Intermediate Similarity	NPD4749	Approved
0.7832	Intermediate Similarity	NPD1610	Phase 2
0.7716	Intermediate Similarity	NPD8455	Phase 2
0.7674	Intermediate Similarity	NPD8312	Approved
0.7674	Intermediate Similarity	NPD8313	Approved
0.7669	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD37	Approved
0.7636	Intermediate Similarity	NPD6234	Discontinued
0.7622	Intermediate Similarity	NPD4966	Approved
0.7622	Intermediate Similarity	NPD4965	Approved
0.7622	Intermediate Similarity	NPD4967	Phase 2
0.7588	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7240	Approved
0.7544	Intermediate Similarity	NPD7074	Phase 3
0.7517	Intermediate Similarity	NPD2861	Phase 2
0.75	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.7484	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD6099	Approved
0.7457	Intermediate Similarity	NPD6559	Discontinued
0.744	Intermediate Similarity	NPD7199	Phase 2
0.7438	Intermediate Similarity	NPD7447	Phase 1
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7405	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4060	Phase 1
0.7384	Intermediate Similarity	NPD5844	Phase 1
0.7384	Intermediate Similarity	NPD7054	Approved
0.7375	Intermediate Similarity	NPD7213	Phase 3
0.7375	Intermediate Similarity	NPD7212	Phase 2
0.7353	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD7472	Approved
0.7338	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6696	Suspended
0.7314	Intermediate Similarity	NPD7808	Phase 3
0.7308	Intermediate Similarity	NPD4108	Discontinued
0.7305	Intermediate Similarity	NPD7768	Phase 2
0.7278	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7041	Phase 2
0.7267	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7783	Phase 2
0.7262	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7251	Discontinued
0.7256	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1091	Approved
0.7209	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD6797	Phase 2
0.7195	Intermediate Similarity	NPD1653	Approved
0.7193	Intermediate Similarity	NPD7229	Phase 3
0.719	Intermediate Similarity	NPD3027	Phase 3
0.7172	Intermediate Similarity	NPD7340	Approved
0.7169	Intermediate Similarity	NPD7411	Suspended
0.7168	Intermediate Similarity	NPD7473	Discontinued
0.7166	Intermediate Similarity	NPD7680	Approved
0.7158	Intermediate Similarity	NPD8151	Discontinued
0.7143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7097	Phase 1
0.7133	Intermediate Similarity	NPD5327	Phase 3
0.7119	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5735	Approved
0.711	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6166	Phase 2
0.711	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7266	Discontinued
0.7093	Intermediate Similarity	NPD6232	Discontinued
0.7083	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3750	Approved
0.7081	Intermediate Similarity	NPD7466	Approved
0.707	Intermediate Similarity	NPD4097	Suspended
0.7066	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7075	Discontinued
0.7051	Intermediate Similarity	NPD4140	Approved
0.7012	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5762	Approved
0.7	Intermediate Similarity	NPD5763	Approved
0.6994	Remote Similarity	NPD3787	Discontinued
0.6984	Remote Similarity	NPD7696	Phase 3
0.6984	Remote Similarity	NPD7697	Approved
0.6984	Remote Similarity	NPD7698	Approved
0.698	Remote Similarity	NPD4626	Approved
0.6978	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3892	Phase 2
0.6974	Remote Similarity	NPD8651	Approved
0.6966	Remote Similarity	NPD1398	Phase 1
0.6962	Remote Similarity	NPD6353	Approved
0.6957	Remote Similarity	NPD7037	Approved
0.6947	Remote Similarity	NPD7870	Phase 2
0.6947	Remote Similarity	NPD7871	Phase 2
0.6946	Remote Similarity	NPD7458	Discontinued
0.6946	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8053	Approved
0.6944	Remote Similarity	NPD8054	Approved
0.6932	Remote Similarity	NPD3818	Discontinued
0.6923	Remote Similarity	NPD4750	Phase 3
0.6923	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5691	Approved
0.6909	Remote Similarity	NPD2532	Approved
0.6909	Remote Similarity	NPD2534	Approved
0.6909	Remote Similarity	NPD2533	Approved
0.6909	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4380	Phase 2
0.6894	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5058	Phase 3
0.6887	Remote Similarity	NPD422	Phase 1
0.6887	Remote Similarity	NPD3705	Approved
0.6883	Remote Similarity	NPD6584	Phase 3
0.6882	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD1465	Phase 2
0.6871	Remote Similarity	NPD7003	Approved
0.6871	Remote Similarity	NPD6671	Approved
0.6867	Remote Similarity	NPD5126	Approved
0.6867	Remote Similarity	NPD5125	Phase 3
0.6852	Remote Similarity	NPD1549	Phase 2
0.6852	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7390	Discontinued
0.6842	Remote Similarity	NPD6823	Phase 2
0.6839	Remote Similarity	NPD7701	Phase 2
0.6836	Remote Similarity	NPD3751	Discontinued
0.6835	Remote Similarity	NPD3620	Phase 2
0.6835	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD6782	Approved
0.6825	Remote Similarity	NPD6777	Approved
0.6825	Remote Similarity	NPD6781	Approved
0.6825	Remote Similarity	NPD6780	Approved
0.6825	Remote Similarity	NPD6778	Approved
0.6825	Remote Similarity	NPD6779	Approved
0.6825	Remote Similarity	NPD6776	Approved
0.6824	Remote Similarity	NPD1934	Approved
0.6813	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD7435	Discontinued
0.6798	Remote Similarity	NPD8156	Discontinued
0.6782	Remote Similarity	NPD5494	Approved
0.6776	Remote Similarity	NPD1611	Approved
0.6771	Remote Similarity	NPD8319	Approved
0.6771	Remote Similarity	NPD8320	Phase 1
0.677	Remote Similarity	NPD3748	Approved
0.6766	Remote Similarity	NPD6090	Discontinued
0.6763	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD3749	Approved
0.6753	Remote Similarity	NPD1283	Approved
0.6746	Remote Similarity	NPD3226	Approved
0.6742	Remote Similarity	NPD8251	Approved
0.6742	Remote Similarity	NPD8099	Discontinued
0.6742	Remote Similarity	NPD8252	Approved
0.674	Remote Similarity	NPD7549	Discontinued
0.6735	Remote Similarity	NPD7801	Approved
0.6731	Remote Similarity	NPD3018	Phase 2
0.6728	Remote Similarity	NPD2438	Suspended
0.6725	Remote Similarity	NPD6801	Discontinued
0.6724	Remote Similarity	NPD5709	Phase 3
0.672	Remote Similarity	NPD7700	Phase 2
0.672	Remote Similarity	NPD7699	Phase 2
0.6709	Remote Similarity	NPD7985	Registered
0.6709	Remote Similarity	NPD7294	Phase 1
0.6709	Remote Similarity	NPD6798	Discontinued
0.6709	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD4536	Approved
0.6708	Remote Similarity	NPD4538	Approved
0.6708	Remote Similarity	NPD7119	Phase 2
0.6688	Remote Similarity	NPD6582	Phase 2
0.6688	Remote Similarity	NPD6583	Phase 3
0.6687	Remote Similarity	NPD6355	Discontinued
0.6687	Remote Similarity	NPD6666	Approved
0.6687	Remote Similarity	NPD6667	Approved
0.6686	Remote Similarity	NPD4666	Phase 3
0.6686	Remote Similarity	NPD5929	Approved
0.6684	Remote Similarity	NPD7874	Approved
0.6684	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6273	Approved
0.6667	Remote Similarity	NPD4624	Approved
0.6667	Remote Similarity	NPD8032	Phase 2
0.6667	Remote Similarity	NPD2342	Discontinued
0.6667	Remote Similarity	NPD7635	Approved
0.6667	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7843	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