NPASS Compound

Structure

NPC274454 OpenBabel07101718302D 41 46 0 0 1 0 0 0 0 0999 V2000 -4.2380 3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 -1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 5.3830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -3.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 5.3830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -2.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 4.4043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 2.4468 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8476 -0.4894 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6952 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6952 3.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 2.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 -1.9574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.9149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 -0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 1.4681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3904 1.9574 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2380 -0.4894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 2.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -2.4468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 2.4468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8476 -0.4894 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 -0.9787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 2.9362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5428 4.4043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2380 -2.4468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8476 4.4043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0856 1.9574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6952 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 37 1 0 0 0 0 4 38 1 0 0 0 0 5 39 1 0 0 0 0 6 14 2 0 0 0 0 6 16 1 0 0 0 0 7 14 1 0 0 0 0 7 20 2 0 0 0 0 8 15 2 0 0 0 0 8 17 1 0 0 0 0 9 15 1 0 0 0 0 9 21 2 0 0 0 0 10 18 1 0 0 0 0 10 40 1 0 0 0 0 11 19 1 0 0 0 0 11 41 1 0 0 0 0 12 1 1 1 0 0 0 12 28 1 0 0 0 0 12 40 1 0 0 0 0 13 2 1 1 0 0 0 13 29 1 0 0 0 0 13 41 1 0 0 0 0 14 32 1 0 0 0 0 15 37 1 0 0 0 0 16 22 2 0 0 0 0 16 24 1 0 0 0 0 17 23 2 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 18 30 2 0 0 0 0 19 27 1 0 0 0 0 19 31 2 0 0 0 0 20 22 1 0 0 0 0 20 38 1 0 0 0 0 21 23 1 0 0 0 0 21 39 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 25 1 0 0 0 0 24 26 2 0 0 0 0 25 27 2 0 0 0 0 26 28 1 0 0 0 0 27 29 1 0 0 0 0 28 33 1 1 0 0 0 29 34 1 1 0 0 0 30 35 1 0 0 0 0 31 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	206.13
Volume:	231.882
LogP:	3.687
LogD:	3.318
LogS:	-3.701
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.822
Synthetic Accessibility Score:	2.192
Fsp3:	0.462
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.377
MDCK Permeability:	3.547169399098493e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.463
Plasma Protein Binding (PPB):	94.36505126953125%
Volume Distribution (VD):	0.238
Pgp-substrate:	3.6475677490234375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.079
CYP1A2-substrate:	0.317
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.91
CYP2C9-inhibitor:	0.416
CYP2C9-substrate:	0.982
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.101
CYP3A4-inhibitor:	0.014
CYP3A4-substrate:	0.195

ADMET: Excretion

Clearance (CL):	0.778
Half-life (T1/2):	0.687

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.431
Drug-inuced Liver Injury (DILI):	0.946
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.538
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.17
Carcinogencity:	0.072
Eye Corrosion:	0.018
Eye Irritation:	0.586
Respiratory Toxicity:	0.066

Download Data

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

Natural Product: NPC274454

Natural Product ID:	NPC274454
*Common Name:**	(3S,4S,3's,4's)-9,7',9'-Trimethoxy-3,3'-Dimethyl-3,4,3',4'-Tetrahydro-1H,1'h-[5,5']Bi[Benzo[G]Isochromenyl]-4,7,10,4',10'-Pentaol
IUPAC Name:	(3S,4S)-5-[(3S,4S)-4,10-dihydroxy-7,9-dimethoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromen-5-yl]-9-methoxy-3-methyl-3,4-dihydro-1H-benzo[g]isochromene-4,7,10-triol
Synonyms:
Standard InCHIKey:	AAAGKEAEOHPDBS-SAAODOGCSA-N
Standard InCHI:	InChI=1S/C31H32O10/c1-12-28(33)26-18(10-40-12)30(35)22-16(6-14(32)7-20(22)38-4)24(26)25-17-8-15(37-3)9-21(39-5)23(17)31(36)19-11-41-13(2)29(34)27(19)25/h6-9,12-13,28-29,32-36H,10-11H2,1-5H3/t12-,13-,28+,29+/m0/s1
SMILES:	COc1cc(OC)c2c(c1)c(c1c3[C@H](O)[C@H](C)OCc3c(c3c1cc(O)cc3OC)O)c1c(c2O)CO[C@H]([C@H]1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251102
PubChem CID:	23657442
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001610] Arylnaphthalene 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
NPO32515	Cordyceps sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17887724]
NPO32514	Cordyceps sp.	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[17887724]

☑ 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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Inhibition	<	50.0	%	PMID[515074]

☑ 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 NPC274454 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	468
0.1-0.2	1587
0.2-0.3	4124
0.3-0.4	10527
0.4-0.5	8215
0.5-0.6	4116
0.6-0.7	7590
0.7-0.8	5143
0.8-0.85	647
0.85-0.9	230
0.9-0.95	46
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC215678
0.9928	High Similarity	NPC153182
0.9928	High Similarity	NPC174251
0.9444	High Similarity	NPC162976
0.9444	High Similarity	NPC118000
0.9444	High Similarity	NPC205501
0.9149	High Similarity	NPC273623
0.911	High Similarity	NPC321657
0.911	High Similarity	NPC318373
0.9085	High Similarity	NPC277331
0.9085	High Similarity	NPC100482
0.9071	High Similarity	NPC472647
0.9071	High Similarity	NPC191462
0.9071	High Similarity	NPC472649
0.9071	High Similarity	NPC170328
0.9071	High Similarity	NPC472648
0.9071	High Similarity	NPC206525
0.9071	High Similarity	NPC133463
0.9034	High Similarity	NPC96576
0.9007	High Similarity	NPC472646
0.9007	High Similarity	NPC71465
0.9	High Similarity	NPC37410
0.9	High Similarity	NPC258780
0.898	High Similarity	NPC211561
0.8973	High Similarity	NPC262297
0.8973	High Similarity	NPC204770
0.8973	High Similarity	NPC236202
0.8973	High Similarity	NPC263940
0.8973	High Similarity	NPC82917
0.8973	High Similarity	NPC70409
0.8973	High Similarity	NPC108811
0.8973	High Similarity	NPC202742
0.8973	High Similarity	NPC58190
0.8973	High Similarity	NPC18185
0.8973	High Similarity	NPC262911
0.8973	High Similarity	NPC294558
0.8973	High Similarity	NPC170103
0.8919	High Similarity	NPC477612
0.8904	High Similarity	NPC126291
0.8897	High Similarity	NPC475492
0.8889	High Similarity	NPC186033
0.8889	High Similarity	NPC183709
0.8849	High Similarity	NPC282508
0.8844	High Similarity	NPC474397
0.88	High Similarity	NPC325860
0.88	High Similarity	NPC226809
0.88	High Similarity	NPC279406
0.88	High Similarity	NPC476391
0.8784	High Similarity	NPC20757
0.8784	High Similarity	NPC227516
0.8777	High Similarity	NPC254000
0.8776	High Similarity	NPC102280
0.8776	High Similarity	NPC155564
0.8776	High Similarity	NPC248053
0.8767	High Similarity	NPC28440
0.8767	High Similarity	NPC171932
0.8759	High Similarity	NPC472088
0.8759	High Similarity	NPC472087
0.875	High Similarity	NPC12668
0.875	High Similarity	NPC308768
0.8742	High Similarity	NPC224161
0.8741	High Similarity	NPC22902
0.8741	High Similarity	NPC470308
0.8741	High Similarity	NPC266006
0.8741	High Similarity	NPC470307
0.869	High Similarity	NPC472089
0.869	High Similarity	NPC265075
0.8684	High Similarity	NPC46335
0.8681	High Similarity	NPC105847
0.8681	High Similarity	NPC218131
0.8681	High Similarity	NPC243759
0.8681	High Similarity	NPC114171
0.8681	High Similarity	NPC275061
0.8681	High Similarity	NPC220344
0.8681	High Similarity	NPC6300
0.8681	High Similarity	NPC243996
0.8681	High Similarity	NPC230124
0.8681	High Similarity	NPC132804
0.8675	High Similarity	NPC226108
0.8675	High Similarity	NPC272552
0.8675	High Similarity	NPC469944
0.8675	High Similarity	NPC233467
0.8675	High Similarity	NPC44192
0.8675	High Similarity	NPC46283
0.8675	High Similarity	NPC322899
0.8675	High Similarity	NPC59692
0.8675	High Similarity	NPC134911
0.8671	High Similarity	NPC471522
0.8671	High Similarity	NPC472800
0.8667	High Similarity	NPC260781
0.8667	High Similarity	NPC9933
0.8667	High Similarity	NPC469707
0.8667	High Similarity	NPC214326
0.8667	High Similarity	NPC158784
0.8667	High Similarity	NPC182368
0.8667	High Similarity	NPC218041
0.8667	High Similarity	NPC469706
0.8667	High Similarity	NPC225815
0.8667	High Similarity	NPC145979
0.8667	High Similarity	NPC185955
0.8662	High Similarity	NPC473107
0.8658	High Similarity	NPC281549
0.8658	High Similarity	NPC473876
0.8649	High Similarity	NPC14468
0.8649	High Similarity	NPC233980
0.8639	High Similarity	NPC473108
0.8639	High Similarity	NPC473845
0.8633	High Similarity	NPC38017
0.8633	High Similarity	NPC148366
0.8633	High Similarity	NPC215300
0.8633	High Similarity	NPC311293
0.863	High Similarity	NPC175838
0.8623	High Similarity	NPC82299
0.8621	High Similarity	NPC472090
0.8621	High Similarity	NPC472092
0.8621	High Similarity	NPC472091
0.8618	High Similarity	NPC306267
0.8618	High Similarity	NPC20050
0.8611	High Similarity	NPC56329
0.8611	High Similarity	NPC266453
0.8611	High Similarity	NPC200935
0.8611	High Similarity	NPC151656
0.8611	High Similarity	NPC242715
0.8611	High Similarity	NPC230919
0.8609	High Similarity	NPC302915
0.8609	High Similarity	NPC471403
0.8609	High Similarity	NPC2745
0.8609	High Similarity	NPC259707
0.86	High Similarity	NPC476969
0.86	High Similarity	NPC295573
0.86	High Similarity	NPC470208
0.8582	High Similarity	NPC473309
0.8582	High Similarity	NPC471517
0.8582	High Similarity	NPC103799
0.8582	High Similarity	NPC160623
0.8571	High Similarity	NPC469630
0.8571	High Similarity	NPC471518
0.8571	High Similarity	NPC471519
0.8562	High Similarity	NPC178054
0.8562	High Similarity	NPC157333
0.8561	High Similarity	NPC473221
0.8561	High Similarity	NPC53781
0.8553	High Similarity	NPC21902
0.8553	High Similarity	NPC120633
0.8553	High Similarity	NPC157783
0.8553	High Similarity	NPC473018
0.8552	High Similarity	NPC184613
0.8552	High Similarity	NPC475836
0.8552	High Similarity	NPC32630
0.8551	High Similarity	NPC293801
0.8543	High Similarity	NPC195561
0.8542	High Similarity	NPC143139
0.8542	High Similarity	NPC202846
0.8542	High Similarity	NPC470802
0.8542	High Similarity	NPC30632
0.8542	High Similarity	NPC141717
0.8533	High Similarity	NPC212142
0.8531	High Similarity	NPC476615
0.8531	High Similarity	NPC125649
0.8531	High Similarity	NPC476616
0.8531	High Similarity	NPC476617
0.8523	High Similarity	NPC471608
0.8523	High Similarity	NPC260397
0.8516	High Similarity	NPC4809
0.8516	High Similarity	NPC147743
0.8516	High Similarity	NPC73517
0.8514	High Similarity	NPC50250
0.8514	High Similarity	NPC304894
0.8514	High Similarity	NPC15659
0.85	High Similarity	NPC471064
0.8493	Intermediate Similarity	NPC34431
0.8493	Intermediate Similarity	NPC73505
0.8493	Intermediate Similarity	NPC295719
0.8493	Intermediate Similarity	NPC174787
0.8493	Intermediate Similarity	NPC262189
0.8493	Intermediate Similarity	NPC165026
0.8493	Intermediate Similarity	NPC213607
0.8493	Intermediate Similarity	NPC182509
0.8493	Intermediate Similarity	NPC22317
0.8489	Intermediate Similarity	NPC170485
0.8472	Intermediate Similarity	NPC256262
0.8472	Intermediate Similarity	NPC10314
0.8472	Intermediate Similarity	NPC241241
0.8472	Intermediate Similarity	NPC108198
0.8472	Intermediate Similarity	NPC294884
0.8472	Intermediate Similarity	NPC200557
0.8472	Intermediate Similarity	NPC69029
0.8472	Intermediate Similarity	NPC158142
0.8472	Intermediate Similarity	NPC125579
0.8472	Intermediate Similarity	NPC11727
0.8472	Intermediate Similarity	NPC15109
0.8467	Intermediate Similarity	NPC111134
0.8467	Intermediate Similarity	NPC112819
0.8467	Intermediate Similarity	NPC133209
0.8467	Intermediate Similarity	NPC6702
0.8462	Intermediate Similarity	NPC185231
0.8462	Intermediate Similarity	NPC159526
0.8462	Intermediate Similarity	NPC86630
0.8462	Intermediate Similarity	NPC106601
0.8462	Intermediate Similarity	NPC469610

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 NPC274454 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	393
0.1-0.2	904
0.2-0.3	1842
0.3-0.4	2740
0.4-0.5	1656
0.5-0.6	967
0.6-0.7	539
0.7-0.8	101
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
0.838	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6959	Discontinued
0.831	Intermediate Similarity	NPD4625	Phase 3
0.8239	Intermediate Similarity	NPD4908	Phase 1
0.8138	Intermediate Similarity	NPD1613	Approved
0.8138	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7228	Approved
0.7947	Intermediate Similarity	NPD6674	Discontinued
0.7917	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD8455	Phase 2
0.7862	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7847	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD5844	Phase 1
0.7762	Intermediate Similarity	NPD4749	Approved
0.7746	Intermediate Similarity	NPD1610	Phase 2
0.7688	Intermediate Similarity	NPD37	Approved
0.7673	Intermediate Similarity	NPD4380	Phase 2
0.7669	Intermediate Similarity	NPD6234	Discontinued
0.7654	Intermediate Similarity	NPD4965	Approved
0.7654	Intermediate Similarity	NPD4967	Phase 2
0.7654	Intermediate Similarity	NPD4966	Approved
0.7651	Intermediate Similarity	NPD6166	Phase 2
0.7651	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD6232	Discontinued
0.7605	Intermediate Similarity	NPD7473	Discontinued
0.7602	Intermediate Similarity	NPD8313	Approved
0.7602	Intermediate Similarity	NPD8312	Approved
0.7588	Intermediate Similarity	NPD7240	Approved
0.7551	Intermediate Similarity	NPD2861	Phase 2
0.7546	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD4060	Phase 1
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.7485	Intermediate Similarity	NPD6559	Discontinued
0.7485	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD7447	Phase 1
0.7465	Intermediate Similarity	NPD1548	Phase 1
0.7439	Intermediate Similarity	NPD7768	Phase 2
0.7423	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3620	Phase 2
0.7417	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7041	Phase 2
0.7405	Intermediate Similarity	NPD7212	Phase 2
0.7405	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7213	Phase 3
0.7403	Intermediate Similarity	NPD6099	Approved
0.7403	Intermediate Similarity	NPD6100	Approved
0.7401	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7074	Phase 3
0.7368	Intermediate Similarity	NPD5735	Approved
0.7366	Intermediate Similarity	NPD8151	Discontinued
0.7358	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD8054	Approved
0.7356	Intermediate Similarity	NPD8053	Approved
0.7347	Intermediate Similarity	NPD6696	Suspended
0.7347	Intermediate Similarity	NPD8651	Approved
0.7337	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD3787	Discontinued
0.7317	Intermediate Similarity	NPD7819	Suspended
0.731	Intermediate Similarity	NPD7054	Approved
0.7289	Intermediate Similarity	NPD7075	Discontinued
0.7284	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4538	Approved
0.7273	Intermediate Similarity	NPD4536	Approved
0.7273	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7472	Approved
0.7262	Intermediate Similarity	NPD7199	Phase 2
0.7256	Intermediate Similarity	NPD1934	Approved
0.7255	Intermediate Similarity	NPD5124	Phase 1
0.7255	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD5762	Approved
0.7244	Intermediate Similarity	NPD5763	Approved
0.7244	Intermediate Similarity	NPD7266	Discontinued
0.7241	Intermediate Similarity	NPD5126	Approved
0.7241	Intermediate Similarity	NPD5125	Phase 3
0.7234	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7229	Phase 3
0.7215	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1465	Phase 2
0.7208	Intermediate Similarity	NPD4097	Suspended
0.72	Intermediate Similarity	NPD3018	Phase 2
0.7186	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD7251	Discontinued
0.7181	Intermediate Similarity	NPD3094	Phase 2
0.7161	Intermediate Similarity	NPD7097	Phase 1
0.7158	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7808	Phase 3
0.7143	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2533	Approved
0.7143	Intermediate Similarity	NPD1091	Approved
0.7143	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2534	Approved
0.7143	Intermediate Similarity	NPD2532	Approved
0.7133	Intermediate Similarity	NPD7157	Approved
0.7126	Intermediate Similarity	NPD6797	Phase 2
0.7123	Intermediate Similarity	NPD4626	Approved
0.7117	Intermediate Similarity	NPD1653	Approved
0.7115	Intermediate Similarity	NPD5960	Phase 3
0.7115	Intermediate Similarity	NPD5588	Approved
0.711	Intermediate Similarity	NPD8156	Discontinued
0.7108	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7003	Approved
0.7097	Intermediate Similarity	NPD7680	Approved
0.7091	Intermediate Similarity	NPD7411	Suspended
0.7083	Intermediate Similarity	NPD7340	Approved
0.7076	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4750	Phase 3
0.707	Intermediate Similarity	NPD2438	Suspended
0.7059	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5691	Approved
0.7052	Intermediate Similarity	NPD8252	Approved
0.7052	Intermediate Similarity	NPD8251	Approved
0.7052	Intermediate Similarity	NPD3751	Discontinued
0.7052	Intermediate Similarity	NPD8099	Discontinued
0.705	Intermediate Similarity	NPD2342	Discontinued
0.7047	Intermediate Similarity	NPD5327	Phase 3
0.7047	Intermediate Similarity	NPD2983	Phase 2
0.7047	Intermediate Similarity	NPD2982	Phase 2
0.7044	Intermediate Similarity	NPD1652	Phase 2
0.7043	Intermediate Similarity	NPD6823	Phase 2
0.7042	Intermediate Similarity	NPD7635	Approved
0.7042	Intermediate Similarity	NPD7843	Approved
0.7037	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3092	Approved
0.7027	Intermediate Similarity	NPD6782	Approved
0.7027	Intermediate Similarity	NPD6781	Approved
0.7027	Intermediate Similarity	NPD6780	Approved
0.7027	Intermediate Similarity	NPD6778	Approved
0.7027	Intermediate Similarity	NPD6779	Approved
0.7027	Intermediate Similarity	NPD6777	Approved
0.7027	Intermediate Similarity	NPD6776	Approved
0.7025	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5058	Phase 3
0.7016	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7783	Phase 2
0.7014	Intermediate Similarity	NPD6671	Approved
0.7006	Intermediate Similarity	NPD5929	Approved
0.7005	Intermediate Similarity	NPD7435	Discontinued
0.7005	Intermediate Similarity	NPD7696	Phase 3
0.7005	Intermediate Similarity	NPD7697	Approved
0.7005	Intermediate Similarity	NPD7698	Approved
0.7	Intermediate Similarity	NPD7466	Approved
0.7	Intermediate Similarity	NPD5494	Approved
0.7	Intermediate Similarity	NPD3892	Phase 2
0.7	Intermediate Similarity	NPD3750	Approved
0.7	Intermediate Similarity	NPD4666	Phase 3
0.6993	Remote Similarity	NPD1398	Phase 1
0.6988	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7037	Approved
0.698	Remote Similarity	NPD2981	Phase 2
0.697	Remote Similarity	NPD4005	Discontinued
0.6968	Remote Similarity	NPD2238	Phase 2
0.6968	Remote Similarity	NPD4140	Approved
0.6968	Remote Similarity	NPD7870	Phase 2
0.6968	Remote Similarity	NPD7871	Phase 2
0.6962	Remote Similarity	NPD5408	Approved
0.6962	Remote Similarity	NPD5406	Approved
0.6962	Remote Similarity	NPD5405	Approved
0.6962	Remote Similarity	NPD5404	Approved
0.6957	Remote Similarity	NPD2677	Approved
0.6948	Remote Similarity	NPD6798	Discontinued
0.6947	Remote Similarity	NPD7701	Phase 2
0.6946	Remote Similarity	NPD6801	Discontinued
0.6944	Remote Similarity	NPD7906	Approved
0.6941	Remote Similarity	NPD5709	Phase 3
0.6939	Remote Similarity	NPD1651	Approved
0.6927	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD3705	Approved
0.6913	Remote Similarity	NPD1611	Approved
0.6908	Remote Similarity	NPD6584	Phase 3
0.6905	Remote Similarity	NPD2801	Approved
0.6901	Remote Similarity	NPD6746	Phase 2
0.6899	Remote Similarity	NPD4108	Discontinued
0.6894	Remote Similarity	NPD4628	Phase 3
0.6892	Remote Similarity	NPD5846	Approved
0.6892	Remote Similarity	NPD6516	Phase 2
0.6889	Remote Similarity	NPD8150	Discontinued
0.6887	Remote Similarity	NPD1283	Approved
0.6883	Remote Similarity	NPD7095	Approved
0.6882	Remote Similarity	NPD7975	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD3749	Approved
0.6879	Remote Similarity	NPD2684	Approved
0.6879	Remote Similarity	NPD6353	Approved
0.6875	Remote Similarity	NPD2424	Discontinued
0.6875	Remote Similarity	NPD1549	Phase 2
0.6875	Remote Similarity	NPD970	Clinical (unspecified phase)

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