NPASS Compound

Structure

CID253722 OpenBabel06191716052D 27 29 0 0 1 0 0 0 0 0999 V2000 2.0981 6.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2509 2.5568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6473 2.4373 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3164 3.1805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9344 1.2784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2872 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 3.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9563 1.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 1.5388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0981 4.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2946 2.9726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 4.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6036 2.0215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9641 4.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9637 3.7157 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9781 1.6942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 5.5388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5817 1.8136 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 25 1 0 0 0 0 2 26 1 0 0 0 0 3 5 2 0 0 0 0 3 12 1 0 0 0 0 4 6 2 0 0 0 0 4 13 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 12 1 0 0 0 0 7 14 1 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 18 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 27 1 0 0 0 0 14 20 1 6 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 23 2 0 0 0 0 19 27 1 0 0 0 0 20 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.14
Volume:	371.883
LogP:	2.206
LogD:	2.429
LogS:	-3.821
# Rotatable Bonds:	6
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.662
Synthetic Accessibility Score:	3.363
Fsp3:	0.35
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.857
MDCK Permeability:	1.1710125363606494e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.362
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.156
30% Bioavailability (F30%):	0.214

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.086
Plasma Protein Binding (PPB):	96.30852508544922%
Volume Distribution (VD):	0.622
Pgp-substrate:	4.629123210906982%

ADMET: Metabolism

CYP1A2-inhibitor:	0.775
CYP1A2-substrate:	0.685
CYP2C19-inhibitor:	0.727
CYP2C19-substrate:	0.489
CYP2C9-inhibitor:	0.774
CYP2C9-substrate:	0.827
CYP2D6-inhibitor:	0.675
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.898
CYP3A4-substrate:	0.715

ADMET: Excretion

Clearance (CL):	14.884
Half-life (T1/2):	0.859

ADMET: Toxicity

hERG Blockers:	0.067
Human Hepatotoxicity (H-HT):	0.37
Drug-inuced Liver Injury (DILI):	0.184
AMES Toxicity:	0.174
Rat Oral Acute Toxicity:	0.141
Maximum Recommended Daily Dose:	0.476
Skin Sensitization:	0.483
Carcinogencity:	0.723
Eye Corrosion:	0.003
Eye Irritation:	0.72
Respiratory Toxicity:	0.027

Download Data

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

Natural Product: NPC253722

Natural Product ID:	NPC253722
*Common Name:**	(-)-8-Epinortrachelogenin
IUPAC Name:	(3S,4R)-3-hydroxy-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Synonyms:
Standard InCHIKey:	ZITBJWXLODLDRH-VLIAUNLRSA-N
Standard InCHI:	InChI=1S/C20H22O7/c1-25-17-8-12(3-5-15(17)21)7-14-11-27-19(23)20(14,24)10-13-4-6-16(22)18(9-13)26-2/h3-6,8-9,14,21-22,24H,7,10-11H2,1-2H3/t14-,20+/m1/s1
SMILES:	COc1cc(ccc1O)C[C@@H]1COC(=O)[C@]1(O)Cc1ccc(c(c1)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3098864
PubChem CID:	321311
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003686] Furanoid lignans [CHEMONTID:0001604] Tetrahydrofuran lignans [CHEMONTID:0003424] 9,9'-epoxylignans [CHEMONTID:0001613] Dibenzylbutyrolactone lignans

*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
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[15473660]
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15730260]
NPO12068	Firmiana simplex	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124753]
NPO2669	Bowdichia virgilioides	Species	Fabaceae	Eukaryota	n.a.	xylem	n.a.	PMID[16286304]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	stem bark	Kunming, Yunnan Province, China	n.a.	PMID[18986199]
NPO31082	Pulsatilla koreana	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24360605]
NPO2669	Bowdichia virgilioides	Species	Fabaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[29182338]
NPO2905	Tinospora hainanensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12068	Firmiana simplex	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12068	Firmiana simplex	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2905	Tinospora hainanensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9947	Teucrium scorodonia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12068	Firmiana simplex	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1406	Centaurea zuccariniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10211	Pajanelia multijuga	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO8962	Cousinia canescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2905	Tinospora hainanensis	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1255	Waitzia acuminata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5752	Pholas dactylus	Species	Pholadidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3463	Wrightia tinctoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12068	Firmiana simplex	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4037	Veronica anagallis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4844	Acacia simplicifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2669	Bowdichia virgilioides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8443	Uvaria microcarpa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8140	Nauclea parva	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21329	Ilyonectria destructans	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5365	Tetradenia glauca	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9947	Teucrium scorodonia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6937	Xylaria hypoxylon	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21689	Titanotrichum oldhamii	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1886	Cell Line	J774	Mus musculus	IC50	=	14000.0	nM	PMID[523211]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[523210]

☑ 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 NPC253722 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	299
0.1-0.2	1171
0.2-0.3	2781
0.3-0.4	6672
0.4-0.5	11486
0.5-0.6	4477
0.6-0.7	9002
0.7-0.8	6102
0.8-0.85	555
0.85-0.9	122
0.9-0.95	25
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC31751
1.0	High Similarity	NPC253481
0.9559	High Similarity	NPC147379
0.9493	High Similarity	NPC273657
0.9493	High Similarity	NPC106920
0.9489	High Similarity	NPC100675
0.9478	High Similarity	NPC176814
0.9478	High Similarity	NPC300776
0.9478	High Similarity	NPC5310
0.9478	High Similarity	NPC68779
0.9478	High Similarity	NPC4982
0.9357	High Similarity	NPC223185
0.9353	High Similarity	NPC477696
0.9353	High Similarity	NPC470811
0.9353	High Similarity	NPC477697
0.927	High Similarity	NPC281780
0.9197	High Similarity	NPC90431
0.9197	High Similarity	NPC471988
0.9191	High Similarity	NPC67247
0.9124	High Similarity	NPC113295
0.9116	High Similarity	NPC38699
0.9097	High Similarity	NPC216223
0.9097	High Similarity	NPC145569
0.9071	High Similarity	NPC166137
0.9071	High Similarity	NPC29599
0.9071	High Similarity	NPC282291
0.9054	High Similarity	NPC163635
0.9007	High Similarity	NPC52664
0.9	High Similarity	NPC289690
0.9	High Similarity	NPC288452
0.8986	High Similarity	NPC211386
0.8966	High Similarity	NPC668
0.8966	High Similarity	NPC293757
0.8966	High Similarity	NPC174512
0.8966	High Similarity	NPC125570
0.8966	High Similarity	NPC477695
0.8966	High Similarity	NPC474965
0.8958	High Similarity	NPC143892
0.8958	High Similarity	NPC283081
0.8958	High Similarity	NPC221383
0.8958	High Similarity	NPC299090
0.8955	High Similarity	NPC223807
0.8912	High Similarity	NPC476434
0.8857	High Similarity	NPC308976
0.8851	High Similarity	NPC61604
0.8851	High Similarity	NPC473236
0.8851	High Similarity	NPC299706
0.8851	High Similarity	NPC245615
0.8851	High Similarity	NPC115466
0.8849	High Similarity	NPC72796
0.8849	High Similarity	NPC44245
0.8849	High Similarity	NPC470990
0.8844	High Similarity	NPC477700
0.8832	High Similarity	NPC277804
0.8824	High Similarity	NPC241354
0.8819	High Similarity	NPC53884
0.8819	High Similarity	NPC258671
0.8806	High Similarity	NPC280767
0.8792	High Similarity	NPC477299
0.8784	High Similarity	NPC267091
0.8784	High Similarity	NPC95498
0.8784	High Similarity	NPC477699
0.8784	High Similarity	NPC246566
0.8768	High Similarity	NPC181049
0.8768	High Similarity	NPC207400
0.8759	High Similarity	NPC64201
0.8759	High Similarity	NPC174495
0.8759	High Similarity	NPC98356
0.8759	High Similarity	NPC153739
0.8759	High Similarity	NPC145305
0.8759	High Similarity	NPC241522
0.8759	High Similarity	NPC187998
0.8759	High Similarity	NPC242807
0.8759	High Similarity	NPC42300
0.8759	High Similarity	NPC77040
0.8759	High Similarity	NPC257582
0.8759	High Similarity	NPC92164
0.8759	High Similarity	NPC3982
0.875	High Similarity	NPC27159
0.875	High Similarity	NPC128208
0.875	High Similarity	NPC304956
0.875	High Similarity	NPC11258
0.875	High Similarity	NPC21867
0.875	High Similarity	NPC282703
0.875	High Similarity	NPC184733
0.875	High Similarity	NPC45774
0.875	High Similarity	NPC129570
0.8741	High Similarity	NPC131971
0.8741	High Similarity	NPC67467
0.8725	High Similarity	NPC178574
0.8725	High Similarity	NPC65591
0.8725	High Similarity	NPC44730
0.8716	High Similarity	NPC243891
0.8716	High Similarity	NPC32079
0.8696	High Similarity	NPC7171
0.8696	High Similarity	NPC161557
0.8696	High Similarity	NPC115207
0.8696	High Similarity	NPC158079
0.8696	High Similarity	NPC228346
0.8696	High Similarity	NPC27843
0.8696	High Similarity	NPC40432
0.8686	High Similarity	NPC475875
0.8676	High Similarity	NPC5428
0.8675	High Similarity	NPC478055
0.8667	High Similarity	NPC103197
0.8667	High Similarity	NPC257589
0.8667	High Similarity	NPC136757
0.8667	High Similarity	NPC30009
0.8667	High Similarity	NPC53305
0.8662	High Similarity	NPC284409
0.8657	High Similarity	NPC317769
0.8657	High Similarity	NPC31344
0.8649	High Similarity	NPC158635
0.8649	High Similarity	NPC229882
0.8639	High Similarity	NPC236166
0.8639	High Similarity	NPC1580
0.8639	High Similarity	NPC98009
0.8633	High Similarity	NPC4940
0.8621	High Similarity	NPC160378
0.8613	High Similarity	NPC226661
0.8613	High Similarity	NPC470084
0.8611	High Similarity	NPC176586
0.8611	High Similarity	NPC210354
0.8603	High Similarity	NPC92207
0.8603	High Similarity	NPC127937
0.8601	High Similarity	NPC322021
0.8582	High Similarity	NPC152209
0.8581	High Similarity	NPC134047
0.8581	High Similarity	NPC173729
0.8581	High Similarity	NPC272750
0.8581	High Similarity	NPC223006
0.8571	High Similarity	NPC129889
0.8571	High Similarity	NPC155209
0.8571	High Similarity	NPC168799
0.8571	High Similarity	NPC158331
0.8571	High Similarity	NPC205915
0.8571	High Similarity	NPC307006
0.8562	High Similarity	NPC163898
0.8561	High Similarity	NPC318799
0.8561	High Similarity	NPC198388
0.8561	High Similarity	NPC469480
0.8542	High Similarity	NPC470991
0.8542	High Similarity	NPC9218
0.854	High Similarity	NPC281020
0.854	High Similarity	NPC118533
0.854	High Similarity	NPC165045
0.8533	High Similarity	NPC56184
0.8533	High Similarity	NPC93498
0.8533	High Similarity	NPC163883
0.8529	High Similarity	NPC148627
0.8523	High Similarity	NPC32197
0.8516	High Similarity	NPC144557
0.8514	High Similarity	NPC472969
0.8511	High Similarity	NPC135127
0.8511	High Similarity	NPC287745
0.8507	High Similarity	NPC194416
0.8507	High Similarity	NPC472271
0.8507	High Similarity	NPC177291
0.8503	High Similarity	NPC474799
0.85	High Similarity	NPC239302
0.85	High Similarity	NPC18074
0.85	High Similarity	NPC61
0.85	High Similarity	NPC25581
0.85	High Similarity	NPC5419
0.85	High Similarity	NPC175067
0.85	High Similarity	NPC204215
0.85	High Similarity	NPC471505
0.8497	Intermediate Similarity	NPC115281
0.8497	Intermediate Similarity	NPC181168
0.8497	Intermediate Similarity	NPC163527
0.8497	Intermediate Similarity	NPC143328
0.8493	Intermediate Similarity	NPC46161
0.8493	Intermediate Similarity	NPC177644
0.8493	Intermediate Similarity	NPC239608
0.8493	Intermediate Similarity	NPC191158
0.8489	Intermediate Similarity	NPC65935
0.8489	Intermediate Similarity	NPC123196
0.8489	Intermediate Similarity	NPC215941
0.8489	Intermediate Similarity	NPC137427
0.8489	Intermediate Similarity	NPC319282
0.8489	Intermediate Similarity	NPC275724
0.8489	Intermediate Similarity	NPC311419
0.8489	Intermediate Similarity	NPC244246
0.8489	Intermediate Similarity	NPC142985
0.8483	Intermediate Similarity	NPC151423
0.8483	Intermediate Similarity	NPC40237
0.8477	Intermediate Similarity	NPC146277
0.8477	Intermediate Similarity	NPC19380
0.8472	Intermediate Similarity	NPC156709
0.8472	Intermediate Similarity	NPC203351
0.8472	Intermediate Similarity	NPC179505
0.8467	Intermediate Similarity	NPC213552
0.8467	Intermediate Similarity	NPC300329
0.8467	Intermediate Similarity	NPC90128
0.8467	Intermediate Similarity	NPC120225
0.8467	Intermediate Similarity	NPC206882
0.8467	Intermediate Similarity	NPC84076
0.8467	Intermediate Similarity	NPC303680
0.8456	Intermediate Similarity	NPC476394
0.8456	Intermediate Similarity	NPC98809

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 NPC253722 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	761
0.2-0.3	1565
0.3-0.4	2447
0.4-0.5	2126
0.5-0.6	1135
0.6-0.7	723
0.7-0.8	135
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
0.8442	Intermediate Similarity	NPD6234	Discontinued
0.8311	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.831	Intermediate Similarity	NPD6355	Discontinued
0.8235	Intermediate Similarity	NPD37	Approved
0.8194	Intermediate Similarity	NPD4966	Approved
0.8194	Intermediate Similarity	NPD3882	Suspended
0.8194	Intermediate Similarity	NPD4967	Phase 2
0.8194	Intermediate Similarity	NPD4965	Approved
0.8176	Intermediate Similarity	NPD6190	Approved
0.8156	Intermediate Similarity	NPD3027	Phase 3
0.8121	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8112	Intermediate Similarity	NPD4060	Phase 1
0.8108	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD4110	Phase 3
0.8075	Intermediate Similarity	NPD7228	Approved
0.8028	Intermediate Similarity	NPD7095	Approved
0.7987	Intermediate Similarity	NPD7199	Phase 2
0.7986	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7972	Intermediate Similarity	NPD6798	Discontinued
0.7917	Intermediate Similarity	NPD6233	Phase 2
0.7914	Intermediate Similarity	NPD1608	Approved
0.7867	Intermediate Similarity	NPD4628	Phase 3
0.7848	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD5283	Phase 1
0.7793	Intermediate Similarity	NPD4062	Phase 3
0.7785	Intermediate Similarity	NPD3817	Phase 2
0.7771	Intermediate Similarity	NPD7685	Pre-registration
0.7771	Intermediate Similarity	NPD1934	Approved
0.7738	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD5958	Discontinued
0.7724	Intermediate Similarity	NPD3764	Approved
0.7724	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2801	Approved
0.7698	Intermediate Similarity	NPD17	Approved
0.7687	Intermediate Similarity	NPD228	Approved
0.7687	Intermediate Similarity	NPD230	Phase 1
0.7677	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1283	Approved
0.7639	Intermediate Similarity	NPD9494	Approved
0.7636	Intermediate Similarity	NPD3818	Discontinued
0.7632	Intermediate Similarity	NPD8166	Discontinued
0.7622	Intermediate Similarity	NPD6166	Phase 2
0.7622	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1613	Approved
0.7619	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD4534	Discontinued
0.761	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD6232	Discontinued
0.76	Intermediate Similarity	NPD2438	Suspended
0.7589	Intermediate Similarity	NPD3705	Approved
0.7586	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7473	Discontinued
0.756	Intermediate Similarity	NPD7240	Approved
0.755	Intermediate Similarity	NPD7266	Discontinued
0.755	Intermediate Similarity	NPD5763	Approved
0.755	Intermediate Similarity	NPD5762	Approved
0.7548	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD3021	Approved
0.7537	Intermediate Similarity	NPD3022	Approved
0.7533	Intermediate Similarity	NPD7033	Discontinued
0.7517	Intermediate Similarity	NPD6653	Approved
0.7517	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1512	Approved
0.75	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1465	Phase 2
0.75	Intermediate Similarity	NPD2797	Approved
0.75	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3620	Phase 2
0.75	Intermediate Similarity	NPD2979	Phase 3
0.7484	Intermediate Similarity	NPD6799	Approved
0.7483	Intermediate Similarity	NPD2935	Discontinued
0.7482	Intermediate Similarity	NPD5536	Phase 2
0.7469	Intermediate Similarity	NPD7075	Discontinued
0.7465	Intermediate Similarity	NPD1281	Approved
0.7448	Intermediate Similarity	NPD5647	Approved
0.7439	Intermediate Similarity	NPD8127	Discontinued
0.7436	Intermediate Similarity	NPD3146	Approved
0.7436	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6004	Phase 3
0.7434	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6005	Phase 3
0.7434	Intermediate Similarity	NPD6002	Phase 3
0.7434	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD1894	Discontinued
0.7421	Intermediate Similarity	NPD6599	Discontinued
0.7421	Intermediate Similarity	NPD7028	Phase 2
0.7403	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD2861	Phase 2
0.7394	Intermediate Similarity	NPD3847	Discontinued
0.7391	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5844	Phase 1
0.7378	Intermediate Similarity	NPD5494	Approved
0.7376	Intermediate Similarity	NPD5585	Approved
0.7375	Intermediate Similarity	NPD6385	Approved
0.7375	Intermediate Similarity	NPD6386	Approved
0.7372	Intermediate Similarity	NPD1511	Approved
0.7365	Intermediate Similarity	NPD3268	Approved
0.7347	Intermediate Similarity	NPD4908	Phase 1
0.7343	Intermediate Similarity	NPD1535	Discovery
0.7338	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7074	Phase 3
0.7333	Intermediate Similarity	NPD447	Suspended
0.7333	Intermediate Similarity	NPD4340	Discontinued
0.7325	Intermediate Similarity	NPD2534	Approved
0.7325	Intermediate Similarity	NPD2533	Approved
0.7325	Intermediate Similarity	NPD2532	Approved
0.7317	Intermediate Similarity	NPD919	Approved
0.7303	Intermediate Similarity	NPD2799	Discontinued
0.7294	Intermediate Similarity	NPD6797	Phase 2
0.7292	Intermediate Similarity	NPD1481	Phase 2
0.729	Intermediate Similarity	NPD3750	Approved
0.7289	Intermediate Similarity	NPD7229	Phase 3
0.7278	Intermediate Similarity	NPD7054	Approved
0.7267	Intermediate Similarity	NPD826	Approved
0.7267	Intermediate Similarity	NPD825	Approved
0.7267	Intermediate Similarity	NPD1558	Phase 1
0.7261	Intermediate Similarity	NPD4357	Discontinued
0.726	Intermediate Similarity	NPD987	Approved
0.7257	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD2531	Phase 2
0.7255	Intermediate Similarity	NPD6099	Approved
0.7255	Intermediate Similarity	NPD6100	Approved
0.7254	Intermediate Similarity	NPD1357	Approved
0.7254	Intermediate Similarity	NPD1651	Approved
0.7251	Intermediate Similarity	NPD7251	Discontinued
0.725	Intermediate Similarity	NPD3455	Phase 2
0.7248	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3926	Phase 2
0.7246	Intermediate Similarity	NPD5242	Approved
0.7241	Intermediate Similarity	NPD2982	Phase 2
0.7241	Intermediate Similarity	NPD2983	Phase 2
0.7241	Intermediate Similarity	NPD8434	Phase 2
0.7239	Intermediate Similarity	NPD5402	Approved
0.7237	Intermediate Similarity	NPD7097	Phase 1
0.7235	Intermediate Similarity	NPD7472	Approved
0.7222	Intermediate Similarity	NPD6801	Discontinued
0.7222	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1610	Phase 2
0.7215	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7808	Phase 3
0.7203	Intermediate Similarity	NPD1778	Approved
0.72	Intermediate Similarity	NPD6663	Approved
0.72	Intermediate Similarity	NPD8032	Phase 2
0.7188	Intermediate Similarity	NPD1653	Approved
0.7186	Intermediate Similarity	NPD3787	Discontinued
0.7183	Intermediate Similarity	NPD9545	Approved
0.7178	Intermediate Similarity	NPD8455	Phase 2
0.7178	Intermediate Similarity	NPD5563	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD7819	Suspended
0.7175	Intermediate Similarity	NPD7296	Approved
0.7172	Intermediate Similarity	NPD2981	Phase 2
0.717	Intermediate Similarity	NPD6273	Approved
0.7162	Intermediate Similarity	NPD3018	Phase 2
0.7162	Intermediate Similarity	NPD5736	Approved
0.716	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7680	Approved
0.7152	Intermediate Similarity	NPD4140	Approved
0.7143	Intermediate Similarity	NPD4477	Approved
0.7143	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2629	Approved
0.7143	Intermediate Similarity	NPD4476	Approved
0.7143	Intermediate Similarity	NPD6032	Approved
0.7134	Intermediate Similarity	NPD2354	Approved
0.7125	Intermediate Similarity	NPD5403	Approved
0.7123	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD4359	Approved
0.7122	Intermediate Similarity	NPD5535	Approved
0.7115	Intermediate Similarity	NPD4236	Phase 3
0.7115	Intermediate Similarity	NPD4237	Approved
0.7114	Intermediate Similarity	NPD2614	Approved
0.7099	Intermediate Similarity	NPD4380	Phase 2
0.7097	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1375	Discontinued
0.7092	Intermediate Similarity	NPD7157	Approved
0.7092	Intermediate Similarity	NPD4198	Discontinued
0.7091	Intermediate Similarity	NPD7768	Phase 2
0.7083	Intermediate Similarity	NPD7315	Approved
0.7083	Intermediate Similarity	NPD4626	Approved
0.7081	Intermediate Similarity	NPD3686	Approved
0.7081	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD3687	Approved
0.708	Intermediate Similarity	NPD2684	Approved
0.7078	Intermediate Similarity	NPD1510	Phase 2
0.7055	Intermediate Similarity	NPD6873	Phase 2
0.7052	Intermediate Similarity	NPD6559	Discontinued
0.7049	Intermediate Similarity	NPD2494	Approved
0.7049	Intermediate Similarity	NPD2493	Approved
0.7048	Intermediate Similarity	NPD3749	Approved
0.7039	Intermediate Similarity	NPD1240	Approved
0.7039	Intermediate Similarity	NPD943	Approved
0.7037	Intermediate Similarity	NPD7458	Discontinued
0.7032	Intermediate Similarity	NPD1551	Phase 2
0.703	Intermediate Similarity	NPD5353	Approved
0.7027	Intermediate Similarity	NPD4582	Approved
0.7027	Intermediate Similarity	NPD3266	Approved
0.7027	Intermediate Similarity	NPD4583	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