NPASS Compound

Structure

CID139540 OpenBabel06191715492D 33 37 0 0 1 0 0 0 0 0999 V2000 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 3 2 0 0 0 0 1 11 1 0 0 0 0 2 4 2 0 0 0 0 2 12 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 11 2 0 0 0 0 5 21 1 0 0 0 0 6 12 2 0 0 0 0 6 22 1 0 0 0 0 7 13 1 0 0 0 0 7 16 1 0 0 0 0 8 15 1 0 0 0 0 8 19 1 0 0 0 0 9 14 1 0 0 0 0 9 24 1 0 0 0 0 10 20 2 0 0 0 0 10 23 1 0 0 0 0 13 11 1 1 0 0 0 13 19 1 0 0 0 0 14 12 1 6 0 0 0 14 25 1 0 0 0 0 15 16 2 0 0 0 0 15 20 1 0 0 0 0 16 25 1 0 0 0 0 17 21 2 0 0 0 0 17 26 1 0 0 0 0 18 22 2 0 0 0 0 18 27 1 0 0 0 0 19 28 1 1 0 0 0 20 29 1 0 0 0 0 21 30 1 0 0 0 0 22 31 1 0 0 0 0 23 25 2 0 0 0 0 23 33 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.13
Volume:	442.131
LogP:	2.966
LogD:	1.835
LogS:	-4.271
# Rotatable Bonds:	2
TPSA:	147.68
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.198
Synthetic Accessibility Score:	4.039
Fsp3:	0.24
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.033
MDCK Permeability:	4.824641109735239e-06
Pgp-inhibitor:	0.019
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.051
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	92.08414459228516%
Volume Distribution (VD):	0.469
Pgp-substrate:	5.535008430480957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.047
CYP1A2-substrate:	0.236
CYP2C19-inhibitor:	0.043
CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.675
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.03
CYP2D6-substrate:	0.228
CYP3A4-inhibitor:	0.131
CYP3A4-substrate:	0.564

ADMET: Excretion

Clearance (CL):	20.708
Half-life (T1/2):	0.895

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.047
Drug-inuced Liver Injury (DILI):	0.38
AMES Toxicity:	0.546
Rat Oral Acute Toxicity:	0.872
Maximum Recommended Daily Dose:	0.988
Skin Sensitization:	0.954
Carcinogencity:	0.274
Eye Corrosion:	0.003
Eye Irritation:	0.889
Respiratory Toxicity:	0.542

Download Data

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

Natural Product: NPC139540

Natural Product ID:	NPC139540
*Common Name:**	Cinchonain I B
IUPAC Name:	(1S,8R,9R)-1,9-bis(3,4-dihydroxyphenyl)-6,8-dihydroxy-1,2,7,8,9,10-hexahydrobenzo[f]chromen-3-one
Synonyms:
Standard InCHIKey:	DKTDHUGOEJFFSN-BIENJYKASA-N
Standard InCHI:	InChI=1S/C25H22O8/c26-17-3-1-11(5-21(17)30)13-7-16-15(8-19(13)28)20(29)10-23-25(16)14(9-24(32)33-23)12-2-4-18(27)22(31)6-12/h1-6,10,13-14,19,26-31H,7-9H2/t13-,14+,19-/m1/s1
SMILES:	O=C1Oc2cc(O)c3c(c2[C@@H](C1)c1ccc(c(c1)O)O)C[C@@H]([C@@H](C3)O)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489954
PubChem CID:	44575964
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001614] Neoflavonoids [CHEMONTID:0003650] Prenylated neoflavonoids

*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
NPO23925	Iryanthera megistophylla	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398535]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	stems	n.a.	n.a.	PMID[16252910]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7132	Smilax glabra	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23925	Iryanthera megistophylla	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25611	Smilax china	Species	Smilacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7132	Smilax glabra	Species	Smilacaceae	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
MIC	2
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1105	Organism	Potato virus X	Potato virus X	Inhibition	=	100.0	%	PMID[529634]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	MIC	=	20.0	ug.mL-1	PMID[529634]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	150.0	ug.mL-1	PMID[529634]

☑ 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 NPC139540 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	384
0.1-0.2	1601
0.2-0.3	3585
0.3-0.4	8778
0.4-0.5	9788
0.5-0.6	3679
0.6-0.7	5456
0.7-0.8	8137
0.8-0.85	1134
0.85-0.9	143
0.9-0.95	3
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC177100
0.961	High Similarity	NPC98083
0.961	High Similarity	NPC7543
0.961	High Similarity	NPC24339
0.961	High Similarity	NPC166456
0.961	High Similarity	NPC94220
0.9487	High Similarity	NPC109061
0.9481	High Similarity	NPC165483
0.9371	High Similarity	NPC9309
0.9363	High Similarity	NPC124747
0.9363	High Similarity	NPC155754
0.8938	High Similarity	NPC24164
0.8909	High Similarity	NPC65333
0.8902	High Similarity	NPC300307
0.8868	High Similarity	NPC318432
0.8861	High Similarity	NPC268484
0.8855	High Similarity	NPC98583
0.8827	High Similarity	NPC55121
0.8817	High Similarity	NPC53680
0.8817	High Similarity	NPC208797
0.8812	High Similarity	NPC114179
0.8812	High Similarity	NPC156818
0.8812	High Similarity	NPC68324
0.8812	High Similarity	NPC289322
0.8812	High Similarity	NPC160512
0.8812	High Similarity	NPC38779
0.8797	High Similarity	NPC223720
0.8797	High Similarity	NPC178574
0.8797	High Similarity	NPC65591
0.8795	High Similarity	NPC4200
0.8795	High Similarity	NPC100251
0.878	High Similarity	NPC171985
0.878	High Similarity	NPC224851
0.878	High Similarity	NPC320741
0.8774	High Similarity	NPC58190
0.8774	High Similarity	NPC70409
0.8774	High Similarity	NPC263940
0.8774	High Similarity	NPC170103
0.8774	High Similarity	NPC18185
0.8774	High Similarity	NPC204770
0.8774	High Similarity	NPC82917
0.8774	High Similarity	NPC202742
0.8774	High Similarity	NPC108811
0.8774	High Similarity	NPC262911
0.8774	High Similarity	NPC294558
0.8774	High Similarity	NPC236202
0.875	High Similarity	NPC300845
0.875	High Similarity	NPC88803
0.875	High Similarity	NPC250436
0.875	High Similarity	NPC291948
0.875	High Similarity	NPC104983
0.8742	High Similarity	NPC8712
0.8735	High Similarity	NPC180768
0.8735	High Similarity	NPC91043
0.8727	High Similarity	NPC473818
0.8721	High Similarity	NPC105591
0.8718	High Similarity	NPC20757
0.8718	High Similarity	NPC227516
0.8718	High Similarity	NPC142863
0.8712	High Similarity	NPC174311
0.871	High Similarity	NPC96576
0.8706	High Similarity	NPC125352
0.8704	High Similarity	NPC53889
0.8696	High Similarity	NPC36077
0.8688	High Similarity	NPC292385
0.8688	High Similarity	NPC125709
0.8683	High Similarity	NPC289396
0.8683	High Similarity	NPC81332
0.8683	High Similarity	NPC212038
0.8683	High Similarity	NPC186847
0.8683	High Similarity	NPC271848
0.8683	High Similarity	NPC257667
0.8683	High Similarity	NPC262580
0.8683	High Similarity	NPC472454
0.8679	High Similarity	NPC474656
0.8675	High Similarity	NPC188079
0.8675	High Similarity	NPC107627
0.8667	High Similarity	NPC471823
0.8662	High Similarity	NPC211561
0.8655	High Similarity	NPC123259
0.8655	High Similarity	NPC129533
0.865	High Similarity	NPC142252
0.8647	High Similarity	NPC80956
0.8642	High Similarity	NPC87317
0.8642	High Similarity	NPC36354
0.8639	High Similarity	NPC297574
0.8627	High Similarity	NPC178054
0.8623	High Similarity	NPC313304
0.8616	High Similarity	NPC44192
0.8616	High Similarity	NPC469944
0.8616	High Similarity	NPC226108
0.8616	High Similarity	NPC272552
0.8616	High Similarity	NPC46283
0.8616	High Similarity	NPC134911
0.8616	High Similarity	NPC322899
0.8614	High Similarity	NPC215802
0.8614	High Similarity	NPC167231
0.8608	High Similarity	NPC477612
0.8606	High Similarity	NPC142614
0.8606	High Similarity	NPC471788
0.8598	High Similarity	NPC192258
0.8598	High Similarity	NPC12326
0.8598	High Similarity	NPC476200
0.8598	High Similarity	NPC476371
0.8598	High Similarity	NPC476372
0.8598	High Similarity	NPC140346
0.859	High Similarity	NPC268515
0.859	High Similarity	NPC40222
0.8589	High Similarity	NPC321399
0.8589	High Similarity	NPC292863
0.8589	High Similarity	NPC184326
0.8589	High Similarity	NPC24627
0.8581	High Similarity	NPC15659
0.8581	High Similarity	NPC304894
0.8571	High Similarity	NPC155015
0.8571	High Similarity	NPC142479
0.8563	High Similarity	NPC269046
0.8563	High Similarity	NPC475212
0.8562	High Similarity	NPC306267
0.8562	High Similarity	NPC20050
0.8554	High Similarity	NPC13481
0.8554	High Similarity	NPC207575
0.8545	High Similarity	NPC476295
0.8545	High Similarity	NPC121290
0.8545	High Similarity	NPC290160
0.8545	High Similarity	NPC67959
0.8545	High Similarity	NPC116759
0.8545	High Similarity	NPC14294
0.8545	High Similarity	NPC45943
0.8538	High Similarity	NPC473785
0.8537	High Similarity	NPC18380
0.8537	High Similarity	NPC186228
0.8537	High Similarity	NPC137232
0.8537	High Similarity	NPC97812
0.8529	High Similarity	NPC67629
0.8529	High Similarity	NPC79736
0.8528	High Similarity	NPC210459
0.8528	High Similarity	NPC117418
0.8528	High Similarity	NPC195167
0.8528	High Similarity	NPC85121
0.8528	High Similarity	NPC53545
0.8516	High Similarity	NPC173203
0.8516	High Similarity	NPC163508
0.8512	High Similarity	NPC102277
0.8512	High Similarity	NPC476365
0.8512	High Similarity	NPC279209
0.8509	High Similarity	NPC62903
0.8509	High Similarity	NPC7178
0.8506	High Similarity	NPC265075
0.8506	High Similarity	NPC237202
0.8503	High Similarity	NPC185498
0.8503	High Similarity	NPC474024
0.8503	High Similarity	NPC217781
0.8503	High Similarity	NPC260266
0.85	High Similarity	NPC279406
0.85	High Similarity	NPC226809
0.85	High Similarity	NPC476391
0.8497	Intermediate Similarity	NPC231254
0.8497	Intermediate Similarity	NPC32630
0.8494	Intermediate Similarity	NPC162169
0.8494	Intermediate Similarity	NPC222531
0.8494	Intermediate Similarity	NPC166851
0.8488	Intermediate Similarity	NPC117668
0.8488	Intermediate Similarity	NPC8940
0.8485	Intermediate Similarity	NPC477841
0.8485	Intermediate Similarity	NPC219927
0.8485	Intermediate Similarity	NPC476247
0.8485	Intermediate Similarity	NPC249070
0.848	Intermediate Similarity	NPC267549
0.848	Intermediate Similarity	NPC207467
0.8476	Intermediate Similarity	NPC476373
0.8476	Intermediate Similarity	NPC301089
0.8476	Intermediate Similarity	NPC268718
0.8476	Intermediate Similarity	NPC150943
0.8476	Intermediate Similarity	NPC119910
0.8476	Intermediate Similarity	NPC36217
0.8476	Intermediate Similarity	NPC91634
0.8466	Intermediate Similarity	NPC264302
0.8466	Intermediate Similarity	NPC125495
0.8462	Intermediate Similarity	NPC67134
0.8462	Intermediate Similarity	NPC473108
0.8462	Intermediate Similarity	NPC171932
0.8462	Intermediate Similarity	NPC47140
0.8462	Intermediate Similarity	NPC28440
0.8457	Intermediate Similarity	NPC142291
0.8457	Intermediate Similarity	NPC321779
0.8457	Intermediate Similarity	NPC67396
0.8457	Intermediate Similarity	NPC173872
0.8457	Intermediate Similarity	NPC7839
0.8457	Intermediate Similarity	NPC119094
0.8452	Intermediate Similarity	NPC476279
0.8448	Intermediate Similarity	NPC112380
0.8447	Intermediate Similarity	NPC224161
0.8447	Intermediate Similarity	NPC476154
0.8443	Intermediate Similarity	NPC43065
0.8443	Intermediate Similarity	NPC49983
0.8443	Intermediate Similarity	NPC317671
0.8443	Intermediate Similarity	NPC142707
0.8443	Intermediate Similarity	NPC472452
0.8443	Intermediate Similarity	NPC26536

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 NPC139540 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	922
0.2-0.3	1806
0.3-0.4	2622
0.4-0.5	1787
0.5-0.6	976
0.6-0.7	519
0.7-0.8	148
0.8-0.85	21
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8788	High Similarity	NPD5844	Phase 1
0.875	High Similarity	NPD4868	Clinical (unspecified phase)
0.8503	High Similarity	NPD7228	Approved
0.8462	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD7199	Phase 2
0.8415	Intermediate Similarity	NPD6234	Discontinued
0.8395	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6166	Phase 2
0.8383	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD37	Approved
0.8313	Intermediate Similarity	NPD6959	Discontinued
0.8293	Intermediate Similarity	NPD4965	Approved
0.8293	Intermediate Similarity	NPD4966	Approved
0.8293	Intermediate Similarity	NPD4967	Phase 2
0.8282	Intermediate Similarity	NPD1465	Phase 2
0.8263	Intermediate Similarity	NPD6232	Discontinued
0.8239	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8225	Intermediate Similarity	NPD7473	Discontinued
0.8214	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD1934	Approved
0.8105	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1613	Approved
0.8081	Intermediate Similarity	NPD7074	Phase 3
0.8061	Intermediate Similarity	NPD8455	Phase 2
0.8061	Intermediate Similarity	NPD7819	Suspended
0.8023	Intermediate Similarity	NPD7054	Approved
0.8012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7240	Approved
0.7988	Intermediate Similarity	NPD4380	Phase 2
0.7977	Intermediate Similarity	NPD7472	Approved
0.7974	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7229	Phase 3
0.7941	Intermediate Similarity	NPD3787	Discontinued
0.7939	Intermediate Similarity	NPD7411	Suspended
0.7931	Intermediate Similarity	NPD6797	Phase 2
0.7927	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7075	Discontinued
0.7898	Intermediate Similarity	NPD8312	Approved
0.7898	Intermediate Similarity	NPD8313	Approved
0.7886	Intermediate Similarity	NPD7251	Discontinued
0.7877	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD3818	Discontinued
0.7857	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD4908	Phase 1
0.7843	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1511	Approved
0.7811	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD3817	Phase 2
0.7778	Intermediate Similarity	NPD8127	Discontinued
0.7778	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3750	Approved
0.7758	Intermediate Similarity	NPD1653	Approved
0.7751	Intermediate Similarity	NPD7768	Phase 2
0.7744	Intermediate Similarity	NPD1512	Approved
0.774	Intermediate Similarity	NPD7808	Phase 3
0.7738	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD2801	Approved
0.7736	Intermediate Similarity	NPD6099	Approved
0.7736	Intermediate Similarity	NPD6100	Approved
0.7719	Intermediate Similarity	NPD5494	Approved
0.7716	Intermediate Similarity	NPD6190	Approved
0.7714	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD3749	Approved
0.7692	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6559	Discontinued
0.7679	Intermediate Similarity	NPD6801	Discontinued
0.7677	Intermediate Similarity	NPD3027	Phase 3
0.766	Intermediate Similarity	NPD7680	Approved
0.7657	Intermediate Similarity	NPD3751	Discontinued
0.7654	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD4060	Phase 1
0.7634	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD5124	Phase 1
0.7593	Intermediate Similarity	NPD6674	Discontinued
0.7593	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2533	Approved
0.7576	Intermediate Similarity	NPD2534	Approved
0.7576	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2532	Approved
0.7576	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD4625	Phase 3
0.7546	Intermediate Similarity	NPD8166	Discontinued
0.7546	Intermediate Similarity	NPD4628	Phase 3
0.7544	Intermediate Similarity	NPD3882	Suspended
0.7531	Intermediate Similarity	NPD1549	Phase 2
0.7531	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6273	Approved
0.7516	Intermediate Similarity	NPD6798	Discontinued
0.75	Intermediate Similarity	NPD3226	Approved
0.75	Intermediate Similarity	NPD1610	Phase 2
0.7485	Intermediate Similarity	NPD5402	Approved
0.7485	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD8151	Discontinued
0.7453	Intermediate Similarity	NPD3748	Approved
0.7439	Intermediate Similarity	NPD7003	Approved
0.741	Intermediate Similarity	NPD7390	Discontinued
0.741	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7097	Phase 1
0.7385	Intermediate Similarity	NPD7783	Phase 2
0.7385	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD5403	Approved
0.7381	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD8150	Discontinued
0.7375	Intermediate Similarity	NPD6355	Discontinued
0.7375	Intermediate Similarity	NPD230	Phase 1
0.7365	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6233	Phase 2
0.7353	Intermediate Similarity	NPD6599	Discontinued
0.7348	Intermediate Similarity	NPD7549	Discontinued
0.7346	Intermediate Similarity	NPD7033	Discontinued
0.7338	Intermediate Similarity	NPD1608	Approved
0.7325	Intermediate Similarity	NPD2861	Phase 2
0.7312	Intermediate Similarity	NPD4140	Approved
0.7308	Intermediate Similarity	NPD2797	Approved
0.7305	Intermediate Similarity	NPD6799	Approved
0.7301	Intermediate Similarity	NPD2438	Suspended
0.7296	Intermediate Similarity	NPD3268	Approved
0.7296	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7458	Discontinued
0.7293	Intermediate Similarity	NPD7685	Pre-registration
0.7292	Intermediate Similarity	NPD7435	Discontinued
0.7278	Intermediate Similarity	NPD7427	Discontinued
0.7263	Intermediate Similarity	NPD7177	Discontinued
0.7262	Intermediate Similarity	NPD5401	Approved
0.7256	Intermediate Similarity	NPD6005	Phase 3
0.7256	Intermediate Similarity	NPD6004	Phase 3
0.7256	Intermediate Similarity	NPD5763	Approved
0.7256	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD7266	Discontinued
0.7256	Intermediate Similarity	NPD5762	Approved
0.7256	Intermediate Similarity	NPD6002	Phase 3
0.7244	Intermediate Similarity	NPD1283	Approved
0.7239	Intermediate Similarity	NPD1510	Phase 2
0.7229	Intermediate Similarity	NPD4110	Phase 3
0.7229	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6779	Approved
0.7225	Intermediate Similarity	NPD6777	Approved
0.7225	Intermediate Similarity	NPD6776	Approved
0.7225	Intermediate Similarity	NPD6781	Approved
0.7225	Intermediate Similarity	NPD6778	Approved
0.7225	Intermediate Similarity	NPD6782	Approved
0.7225	Intermediate Similarity	NPD6780	Approved
0.7205	Intermediate Similarity	NPD2979	Phase 3
0.7195	Intermediate Similarity	NPD1551	Phase 2
0.7195	Intermediate Similarity	NPD5408	Approved
0.7195	Intermediate Similarity	NPD5404	Approved
0.7195	Intermediate Similarity	NPD5406	Approved
0.7195	Intermediate Similarity	NPD2935	Discontinued
0.7195	Intermediate Similarity	NPD2796	Approved
0.7195	Intermediate Similarity	NPD5405	Approved
0.7188	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD4749	Approved
0.7169	Intermediate Similarity	NPD1652	Phase 2
0.716	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD919	Approved
0.7152	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD17	Approved
0.7143	Intermediate Similarity	NPD8032	Phase 2
0.7135	Intermediate Similarity	NPD5711	Approved
0.7135	Intermediate Similarity	NPD5710	Approved
0.7134	Intermediate Similarity	NPD3225	Approved
0.7124	Intermediate Similarity	NPD1548	Phase 1
0.7119	Intermediate Similarity	NPD6746	Phase 2
0.7113	Intermediate Similarity	NPD4004	Approved
0.7113	Intermediate Similarity	NPD4002	Approved
0.7105	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3620	Phase 2
0.7098	Intermediate Similarity	NPD2494	Approved
0.7098	Intermediate Similarity	NPD2493	Approved
0.7098	Intermediate Similarity	NPD3450	Approved
0.7098	Intermediate Similarity	NPD3452	Approved
0.7097	Intermediate Similarity	NPD8434	Phase 2
0.7091	Intermediate Similarity	NPD4476	Approved
0.7091	Intermediate Similarity	NPD4477	Approved
0.7077	Intermediate Similarity	NPD4583	Approved
0.7077	Intermediate Similarity	NPD7870	Phase 2
0.7077	Intermediate Similarity	NPD7871	Phase 2
0.7077	Intermediate Similarity	NPD4582	Approved
0.7074	Intermediate Similarity	NPD2488	Approved
0.7074	Intermediate Similarity	NPD2490	Approved
0.7071	Intermediate Similarity	NPD7874	Approved
0.7071	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD422	Phase 1
0.7051	Intermediate Similarity	NPD1281	Approved
0.7026	Intermediate Similarity	NPD7698	Approved
0.7026	Intermediate Similarity	NPD7697	Approved
0.7026	Intermediate Similarity	NPD7696	Phase 3

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