NPASS Compound

Structure

CID249070 OpenBabel06191716052D 38 41 0 0 1 0 0 0 0 0999 V2000 3.4780 2.5155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9038 0.9265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7637 3.7869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6140 -2.7955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2296 2.9799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6140 -2.7955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8319 -1.0550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8419 1.8636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0349 2.3295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8419 0.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2279 1.8636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0349 0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9318 2.4141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5658 2.9799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6140 -0.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7388 1.9482 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9799 1.0482 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2279 0.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0317 2.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6140 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 2.9799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8070 -1.3977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5658 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8070 0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5140 0.2412 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8319 2.1730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9318 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4209 0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0813 -0.4981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4209 -0.4659 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8319 3.7869 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8070 -2.3295 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7637 2.1730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6140 -1.8636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2978 -0.2480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6140 0.9318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 33 1 0 0 0 0 4 34 1 0 0 0 0 5 35 1 0 0 0 0 6 36 1 0 0 0 0 7 37 1 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 18 2 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 13 19 1 0 0 0 0 14 19 2 0 0 0 0 14 21 1 0 0 0 0 15 20 2 0 0 0 0 15 22 1 0 0 0 0 16 1 1 1 0 0 0 16 17 1 0 0 0 0 17 2 1 1 0 0 0 17 25 1 0 0 0 0 18 30 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 2 0 0 0 0 21 33 1 0 0 0 0 22 27 2 0 0 0 0 22 34 1 0 0 0 0 23 24 1 0 0 0 0 23 28 2 0 0 0 0 24 29 2 0 0 0 0 25 31 1 1 0 0 0 26 28 1 0 0 0 0 26 35 1 0 0 0 0 27 29 1 0 0 0 0 27 36 1 0 0 0 0 28 37 1 0 0 0 0 29 38 1 0 0 0 0 30 32 2 0 0 0 0 30 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	522.23
Volume:	537.167
LogP:	4.6
LogD:	3.952
LogS:	-5.45
# Rotatable Bonds:	8
TPSA:	92.68
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.322
Synthetic Accessibility Score:	3.63
Fsp3:	0.367
Lipinski Rule-of-5:	Accepted
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:	-4.901
MDCK Permeability:	3.806939275818877e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.051

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	83.74092102050781%
Volume Distribution (VD):	0.515
Pgp-substrate:	12.126612663269043%

ADMET: Metabolism

CYP1A2-inhibitor:	0.05
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.675
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.749
CYP2C9-substrate:	0.9
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.728
CYP3A4-inhibitor:	0.504
CYP3A4-substrate:	0.908

ADMET: Excretion

Clearance (CL):	3.506
Half-life (T1/2):	0.247

ADMET: Toxicity

hERG Blockers:	0.121
Human Hepatotoxicity (H-HT):	0.03
Drug-inuced Liver Injury (DILI):	0.427
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.23
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.28
Carcinogencity:	0.011
Eye Corrosion:	0.003
Eye Irritation:	0.095
Respiratory Toxicity:	0.075

Download Data

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

Natural Product: NPC249070

Natural Product ID:	NPC249070
*Common Name:**	Tiegusanin C
IUPAC Name:	n.a.
Synonyms:	Tiegusanin C
Standard InCHIKey:	VQIUJKPVZMSRSS-RYUVBPIJSA-N
Standard InCHI:	InChI=1S/C30H34O8/c1-16-13-19-14-21(33-3)26(35-5)28(37-7)23(19)24-20(25(31)17(16)2)15-22(34-4)27(36-6)29(24)38-30(32)18-11-9-8-10-12-18/h8-12,14-17,25,31H,13H2,1-7H3/t16-,17-,25-/m1/s1
SMILES:	C[C@@H]1Cc2cc(c(c(c2-c2c(cc(c(c2OC(=O)c2ccccc2)OC)OC)[C@@H]([C@@H]1C)O)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL563213
PubChem CID:	44179188
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1002/cjoc.20010190319]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/j.tet.2008.10.079]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[11395273]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[18536373]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	aerial parts	Erlang Mountain area of Sichuan Province, China	2007-SEP	PMID[19413342]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20681569]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7374	Seseli montanum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7850	Schisandra propinqua	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11167	Prunus ssiori	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9834	Veronica austriaca	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6903	Lecanora straminea	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7128	Cynthia savignyi	n.a.	n.a.	n.a.	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
EC50	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	>	200000.0	nM	PMID[521703]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	18500.0	nM	PMID[521703]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	10.8	n.a.	PMID[521703]

☑ 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 NPC249070 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	364
0.1-0.2	1415
0.2-0.3	3254
0.3-0.4	8011
0.4-0.5	10620
0.5-0.6	3348
0.6-0.7	5109
0.7-0.8	8331
0.8-0.85	1972
0.85-0.9	245
0.9-0.95	25
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9675	High Similarity	NPC328122
0.949	High Similarity	NPC473445
0.949	High Similarity	NPC42797
0.943	High Similarity	NPC291977
0.9281	High Similarity	NPC477381
0.9221	High Similarity	NPC477379
0.9193	High Similarity	NPC118162
0.9193	High Similarity	NPC320471
0.9193	High Similarity	NPC83049
0.915	High Similarity	NPC477879
0.9136	High Similarity	NPC311912
0.9103	High Similarity	NPC149735
0.908	High Similarity	NPC88557
0.9062	High Similarity	NPC319749
0.9018	High Similarity	NPC79322
0.8981	High Similarity	NPC475141
0.8961	High Similarity	NPC137352
0.8961	High Similarity	NPC183083
0.8944	High Similarity	NPC191352
0.8944	High Similarity	NPC258322
0.8931	High Similarity	NPC473323
0.8924	High Similarity	NPC473736
0.8916	High Similarity	NPC477881
0.8896	High Similarity	NPC477884
0.8889	High Similarity	NPC280778
0.8889	High Similarity	NPC476371
0.8889	High Similarity	NPC476372
0.8882	High Similarity	NPC24164
0.8882	High Similarity	NPC53889
0.8861	High Similarity	NPC474656
0.8848	High Similarity	NPC476279
0.8846	High Similarity	NPC474347
0.8846	High Similarity	NPC474393
0.8839	High Similarity	NPC295297
0.882	High Similarity	NPC87317
0.8805	High Similarity	NPC473425
0.8795	High Similarity	NPC477883
0.8795	High Similarity	NPC180768
0.879	High Similarity	NPC473091
0.879	High Similarity	NPC470916
0.8765	High Similarity	NPC24627
0.8765	High Similarity	NPC476373
0.8758	High Similarity	NPC160512
0.8758	High Similarity	NPC156818
0.8758	High Similarity	NPC38779
0.8758	High Similarity	NPC289322
0.8758	High Similarity	NPC68324
0.8758	High Similarity	NPC108456
0.8758	High Similarity	NPC114179
0.8757	High Similarity	NPC477882
0.8757	High Similarity	NPC477880
0.875	High Similarity	NPC222185
0.8743	High Similarity	NPC469506
0.8742	High Similarity	NPC24562
0.8727	High Similarity	NPC43065
0.8704	High Similarity	NPC37502
0.8704	High Similarity	NPC230531
0.8704	High Similarity	NPC40702
0.8704	High Similarity	NPC215400
0.8704	High Similarity	NPC267627
0.8698	High Similarity	NPC297574
0.8698	High Similarity	NPC67629
0.8698	High Similarity	NPC79736
0.8696	High Similarity	NPC104983
0.8696	High Similarity	NPC318432
0.8696	High Similarity	NPC469474
0.8696	High Similarity	NPC88803
0.8696	High Similarity	NPC291948
0.8696	High Similarity	NPC300845
0.8696	High Similarity	NPC250436
0.8679	High Similarity	NPC75695
0.8679	High Similarity	NPC228662
0.8679	High Similarity	NPC476434
0.8667	High Similarity	NPC142614
0.8659	High Similarity	NPC476200
0.8659	High Similarity	NPC192258
0.8659	High Similarity	NPC472964
0.8654	High Similarity	NPC474054
0.865	High Similarity	NPC301089
0.8647	High Similarity	NPC267549
0.8642	High Similarity	NPC247713
0.8625	High Similarity	NPC476154
0.8625	High Similarity	NPC477377
0.8606	High Similarity	NPC67959
0.8606	High Similarity	NPC121290
0.8606	High Similarity	NPC475865
0.8598	High Similarity	NPC158188
0.8598	High Similarity	NPC473106
0.8598	High Similarity	NPC103201
0.8598	High Similarity	NPC216916
0.8598	High Similarity	NPC109061
0.8598	High Similarity	NPC469889
0.8596	High Similarity	NPC80956
0.8589	High Similarity	NPC325122
0.8588	High Similarity	NPC473713
0.858	High Similarity	NPC166674
0.858	High Similarity	NPC54928
0.858	High Similarity	NPC46640
0.858	High Similarity	NPC165483
0.858	High Similarity	NPC263119
0.858	High Similarity	NPC219600
0.858	High Similarity	NPC227062
0.858	High Similarity	NPC34436
0.858	High Similarity	NPC477380
0.858	High Similarity	NPC474983
0.8571	High Similarity	NPC43872
0.8571	High Similarity	NPC291510
0.8571	High Similarity	NPC116850
0.8571	High Similarity	NPC238672
0.8571	High Similarity	NPC312763
0.8571	High Similarity	NPC144801
0.8571	High Similarity	NPC476365
0.8571	High Similarity	NPC197188
0.8563	High Similarity	NPC473818
0.8563	High Similarity	NPC471180
0.8562	High Similarity	NPC267091
0.8562	High Similarity	NPC272566
0.8562	High Similarity	NPC477378
0.8562	High Similarity	NPC475229
0.8547	High Similarity	NPC208797
0.8547	High Similarity	NPC53680
0.8545	High Similarity	NPC55121
0.8537	High Similarity	NPC474770
0.8537	High Similarity	NPC472902
0.8537	High Similarity	NPC299436
0.8537	High Similarity	NPC292415
0.8537	High Similarity	NPC119910
0.8535	High Similarity	NPC287275
0.8528	High Similarity	NPC477885
0.8528	High Similarity	NPC183851
0.8528	High Similarity	NPC63454
0.8528	High Similarity	NPC143328
0.8526	High Similarity	NPC87883
0.8521	High Similarity	NPC38438
0.8519	High Similarity	NPC155015
0.8519	High Similarity	NPC142479
0.8519	High Similarity	NPC238834
0.8519	High Similarity	NPC31018
0.8519	High Similarity	NPC476065
0.8519	High Similarity	NPC255807
0.8519	High Similarity	NPC20541
0.8512	High Similarity	NPC99613
0.8512	High Similarity	NPC49487
0.8512	High Similarity	NPC188079
0.8509	High Similarity	NPC16791
0.8509	High Similarity	NPC77237
0.8509	High Similarity	NPC217708
0.8509	High Similarity	NPC308739
0.8509	High Similarity	NPC199773
0.8509	High Similarity	NPC65591
0.8509	High Similarity	NPC178574
0.8509	High Similarity	NPC126405
0.8509	High Similarity	NPC53669
0.8509	High Similarity	NPC297271
0.8503	High Similarity	NPC174734
0.8503	High Similarity	NPC20216
0.8503	High Similarity	NPC474042
0.85	High Similarity	NPC243891
0.85	High Similarity	NPC309979
0.85	High Similarity	NPC475460
0.85	High Similarity	NPC307780
0.8497	Intermediate Similarity	NPC865
0.8494	Intermediate Similarity	NPC134047
0.8494	Intermediate Similarity	NPC300984
0.8494	Intermediate Similarity	NPC223006
0.8494	Intermediate Similarity	NPC272750
0.8494	Intermediate Similarity	NPC474350
0.8494	Intermediate Similarity	NPC173729
0.8494	Intermediate Similarity	NPC45943
0.8491	Intermediate Similarity	NPC107636
0.8485	Intermediate Similarity	NPC139540
0.8485	Intermediate Similarity	NPC177100
0.8485	Intermediate Similarity	NPC349525
0.848	Intermediate Similarity	NPC472723
0.8476	Intermediate Similarity	NPC284127
0.8476	Intermediate Similarity	NPC166456
0.8476	Intermediate Similarity	NPC172202
0.8476	Intermediate Similarity	NPC24339
0.8476	Intermediate Similarity	NPC7543
0.8476	Intermediate Similarity	NPC476410
0.8476	Intermediate Similarity	NPC98083
0.8476	Intermediate Similarity	NPC94220
0.8471	Intermediate Similarity	NPC476374
0.8471	Intermediate Similarity	NPC473550
0.8471	Intermediate Similarity	NPC98583
0.8462	Intermediate Similarity	NPC52598
0.8462	Intermediate Similarity	NPC313304
0.8462	Intermediate Similarity	NPC469630
0.8462	Intermediate Similarity	NPC181778
0.8457	Intermediate Similarity	NPC7178
0.8457	Intermediate Similarity	NPC469888
0.8457	Intermediate Similarity	NPC475895
0.8457	Intermediate Similarity	NPC348849
0.8457	Intermediate Similarity	NPC178134
0.8457	Intermediate Similarity	NPC178195
0.8457	Intermediate Similarity	NPC298802
0.8457	Intermediate Similarity	NPC62903
0.8452	Intermediate Similarity	NPC167231
0.8452	Intermediate Similarity	NPC234331
0.8452	Intermediate Similarity	NPC215802

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 NPC249070 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	904
0.2-0.3	1621
0.3-0.4	2526
0.4-0.5	1914
0.5-0.6	1069
0.6-0.7	586
0.7-0.8	185
0.8-0.85	28
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.908	High Similarity	NPD5844	Phase 1
0.8696	High Similarity	NPD4868	Clinical (unspecified phase)
0.8614	High Similarity	NPD7473	Discontinued
0.8545	High Similarity	NPD6232	Discontinued
0.8457	Intermediate Similarity	NPD1465	Phase 2
0.8395	Intermediate Similarity	NPD37	Approved
0.8373	Intermediate Similarity	NPD7199	Phase 2
0.8354	Intermediate Similarity	NPD4966	Approved
0.8354	Intermediate Similarity	NPD4967	Phase 2
0.8354	Intermediate Similarity	NPD4965	Approved
0.8344	Intermediate Similarity	NPD7819	Suspended
0.8333	Intermediate Similarity	NPD6166	Phase 2
0.8333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8293	Intermediate Similarity	NPD3817	Phase 2
0.8282	Intermediate Similarity	NPD1934	Approved
0.8198	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.8165	Intermediate Similarity	NPD3750	Approved
0.8144	Intermediate Similarity	NPD6234	Discontinued
0.814	Intermediate Similarity	NPD7074	Phase 3
0.8133	Intermediate Similarity	NPD7768	Phase 2
0.8129	Intermediate Similarity	NPD3818	Discontinued
0.8121	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7075	Discontinued
0.8081	Intermediate Similarity	NPD7054	Approved
0.8047	Intermediate Similarity	NPD8127	Discontinued
0.8035	Intermediate Similarity	NPD7472	Approved
0.8023	Intermediate Similarity	NPD7228	Approved
0.8012	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2801	Approved
0.8	Intermediate Similarity	NPD7411	Suspended
0.7988	Intermediate Similarity	NPD5494	Approved
0.7964	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD5402	Approved
0.7962	Intermediate Similarity	NPD3748	Approved
0.7952	Intermediate Similarity	NPD6801	Discontinued
0.7943	Intermediate Similarity	NPD6559	Discontinued
0.7941	Intermediate Similarity	NPD6959	Discontinued
0.7937	Intermediate Similarity	NPD4628	Phase 3
0.7933	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3882	Suspended
0.7898	Intermediate Similarity	NPD7808	Phase 3
0.7898	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD3749	Approved
0.787	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD5403	Approved
0.7853	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7251	Discontinued
0.7831	Intermediate Similarity	NPD4380	Phase 2
0.7818	Intermediate Similarity	NPD1653	Approved
0.7812	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6273	Approved
0.7803	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6799	Approved
0.7791	Intermediate Similarity	NPD1511	Approved
0.7791	Intermediate Similarity	NPD7229	Phase 3
0.7791	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6797	Phase 2
0.7771	Intermediate Similarity	NPD447	Suspended
0.7771	Intermediate Similarity	NPD3226	Approved
0.7753	Intermediate Similarity	NPD8312	Approved
0.7753	Intermediate Similarity	NPD8313	Approved
0.7744	Intermediate Similarity	NPD5401	Approved
0.774	Intermediate Similarity	NPD7240	Approved
0.7725	Intermediate Similarity	NPD6599	Discontinued
0.7719	Intermediate Similarity	NPD919	Approved
0.7716	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1613	Approved
0.7702	Intermediate Similarity	NPD1549	Phase 2
0.7697	Intermediate Similarity	NPD1512	Approved
0.7692	Intermediate Similarity	NPD8455	Phase 2
0.7688	Intermediate Similarity	NPD2796	Approved
0.7667	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD3926	Phase 2
0.764	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7038	Approved
0.764	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7039	Approved
0.7636	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD3027	Phase 3
0.7624	Intermediate Similarity	NPD8434	Phase 2
0.7607	Intermediate Similarity	NPD7003	Approved
0.7598	Intermediate Similarity	NPD7549	Discontinued
0.7597	Intermediate Similarity	NPD2797	Approved
0.758	Intermediate Similarity	NPD6798	Discontinued
0.7578	Intermediate Similarity	NPD1551	Phase 2
0.7578	Intermediate Similarity	NPD2935	Discontinued
0.7571	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4908	Phase 1
0.7564	Intermediate Similarity	NPD6832	Phase 2
0.7561	Intermediate Similarity	NPD6190	Approved
0.7547	Intermediate Similarity	NPD230	Phase 1
0.7547	Intermediate Similarity	NPD6355	Discontinued
0.7542	Intermediate Similarity	NPD7685	Pre-registration
0.753	Intermediate Similarity	NPD2532	Approved
0.753	Intermediate Similarity	NPD2533	Approved
0.753	Intermediate Similarity	NPD2534	Approved
0.7516	Intermediate Similarity	NPD1510	Phase 2
0.7514	Intermediate Similarity	NPD3751	Discontinued
0.7471	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3764	Approved
0.7468	Intermediate Similarity	NPD3268	Approved
0.7468	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD5242	Approved
0.7442	Intermediate Similarity	NPD5353	Approved
0.7442	Intermediate Similarity	NPD4288	Approved
0.7438	Intermediate Similarity	NPD5124	Phase 1
0.7438	Intermediate Similarity	NPD1933	Approved
0.7438	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD2346	Discontinued
0.7421	Intermediate Similarity	NPD6233	Phase 2
0.7407	Intermediate Similarity	NPD4308	Phase 3
0.7407	Intermediate Similarity	NPD2799	Discontinued
0.7394	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD4110	Phase 3
0.7389	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD3787	Discontinued
0.7381	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD4060	Phase 1
0.7375	Intermediate Similarity	NPD1240	Approved
0.7362	Intermediate Similarity	NPD6099	Approved
0.7362	Intermediate Similarity	NPD2438	Suspended
0.7362	Intermediate Similarity	NPD6100	Approved
0.7353	Intermediate Similarity	NPD7458	Discontinued
0.7337	Intermediate Similarity	NPD920	Approved
0.7333	Intermediate Similarity	NPD6674	Discontinued
0.7333	Intermediate Similarity	NPD1652	Phase 2
0.7333	Intermediate Similarity	NPD8151	Discontinued
0.733	Intermediate Similarity	NPD1247	Approved
0.7329	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7177	Discontinued
0.7317	Intermediate Similarity	NPD7266	Discontinued
0.7317	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD1608	Approved
0.7289	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD1607	Approved
0.7277	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6385	Approved
0.7267	Intermediate Similarity	NPD6386	Approved
0.7261	Intermediate Similarity	NPD1203	Approved
0.7259	Intermediate Similarity	NPD7783	Phase 2
0.7259	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6971	Discontinued
0.7256	Intermediate Similarity	NPD5404	Approved
0.7256	Intermediate Similarity	NPD5406	Approved
0.7256	Intermediate Similarity	NPD5405	Approved
0.7256	Intermediate Similarity	NPD5408	Approved
0.7254	Intermediate Similarity	NPD7680	Approved
0.7243	Intermediate Similarity	NPD8150	Discontinued
0.7229	Intermediate Similarity	NPD1243	Approved
0.7228	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1610	Phase 2
0.7226	Intermediate Similarity	NPD422	Phase 1
0.7225	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5762	Approved
0.7212	Intermediate Similarity	NPD5763	Approved
0.7211	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7440	Discontinued
0.7202	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1283	Approved
0.7195	Intermediate Similarity	NPD7033	Discontinued
0.7188	Intermediate Similarity	NPD4625	Phase 3
0.7188	Intermediate Similarity	NPD7095	Approved
0.7186	Intermediate Similarity	NPD8166	Discontinued
0.7179	Intermediate Similarity	NPD9717	Approved
0.7176	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD6746	Phase 2
0.716	Intermediate Similarity	NPD7390	Discontinued
0.716	Intermediate Similarity	NPD4307	Phase 2
0.716	Intermediate Similarity	NPD4140	Approved
0.716	Intermediate Similarity	NPD2979	Phase 3
0.7152	Intermediate Similarity	NPD3266	Approved
0.7152	Intermediate Similarity	NPD3267	Approved
0.7143	Intermediate Similarity	NPD2313	Discontinued
0.7134	Intermediate Similarity	NPD7097	Phase 1
0.7108	Intermediate Similarity	NPD6005	Phase 3
0.7108	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6004	Phase 3
0.7108	Intermediate Similarity	NPD6002	Phase 3
0.7104	Intermediate Similarity	NPD5953	Discontinued
0.7099	Intermediate Similarity	NPD8032	Phase 2
0.7097	Intermediate Similarity	NPD17	Approved
0.7089	Intermediate Similarity	NPD3225	Approved
0.7088	Intermediate Similarity	NPD7286	Phase 2
0.7077	Intermediate Similarity	NPD7435	Discontinued
0.7073	Intermediate Similarity	NPD6653	Approved
0.7063	Intermediate Similarity	NPD3018	Phase 2
0.7063	Intermediate Similarity	NPD2861	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