NPASS Compound

Structure

NPC85047 OpenBabel07101718332D 45 50 0 0 1 0 0 0 0 0999 V2000 -2.4510 -3.3019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8170 -0.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1264 -4.2453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3453 -5.0623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4510 -2.3585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5360 0.9434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0850 -3.3019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9020 -2.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4510 1.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4510 -1.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8170 1.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9020 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6340 -4.7170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4510 -3.3019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2680 -2.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8170 -1.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4510 0.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4510 -4.2453 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9020 -1.8868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2680 -1.8868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6340 -1.8868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.8868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6340 1.8868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8170 0.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7190 -0.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8170 -3.3019 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0850 -0.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8170 0.4717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8170 1.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7190 -1.4151 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8170 -4.2453 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6340 -2.8302 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0850 -1.4151 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2680 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2680 -4.7170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8170 -1.4151 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 2.8302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.8302 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2680 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5360 -1.8868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5360 0.0000 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 17 1 0 0 0 0 2 18 2 0 0 0 0 3 34 1 0 0 0 0 4 34 1 0 0 0 0 6 44 1 0 0 0 0 7 8 1 0 0 0 0 7 17 2 0 0 0 0 8 21 1 0 0 0 0 9 19 2 0 0 0 0 9 25 1 0 0 0 0 10 19 1 0 0 0 0 10 27 2 0 0 0 0 11 22 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 12 29 1 0 0 0 0 13 26 1 0 0 0 0 13 31 2 0 0 0 0 14 28 2 0 0 0 0 14 30 1 0 0 0 0 15 20 1 0 0 0 0 15 34 1 0 0 0 0 16 20 1 0 0 0 0 16 35 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 18 24 1 0 0 0 0 19 37 1 0 0 0 0 20 38 1 6 0 0 0 21 33 1 0 0 0 0 21 36 1 1 0 0 0 22 36 1 6 0 0 0 23 35 1 1 0 0 0 24 39 1 1 0 0 0 25 32 2 0 0 0 0 25 40 1 0 0 0 0 26 32 1 0 0 0 0 26 41 2 0 0 0 0 27 32 1 0 0 0 0 27 45 1 0 0 0 0 28 33 1 0 0 0 0 28 44 1 0 0 0 0 29 34 1 0 0 0 0 29 35 1 1 0 0 0 30 36 1 0 0 0 0 30 42 2 0 0 0 0 31 45 1 0 0 0 0 33 43 2 0 0 0 0 35 5 1 1 0 0 0 36 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	618.28
Volume:	632.621
LogP:	3.424
LogD:	1.962
LogS:	-2.746
# Rotatable Bonds:	4
TPSA:	154.5
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	5.708
Fsp3:	0.528
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:	-5.284
MDCK Permeability:	1.4398605344467796e-05
Pgp-inhibitor:	0.768
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.053
20% Bioavailability (F20%):	0.9
30% Bioavailability (F30%):	0.088

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.174
Plasma Protein Binding (PPB):	87.67855072021484%
Volume Distribution (VD):	1.259
Pgp-substrate:	9.044248580932617%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.503
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.56
CYP2C9-inhibitor:	0.138
CYP2C9-substrate:	0.116
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.776
CYP3A4-substrate:	0.804

ADMET: Excretion

Clearance (CL):	13.21
Half-life (T1/2):	0.415

ADMET: Toxicity

hERG Blockers:	0.367
Human Hepatotoxicity (H-HT):	0.409
Drug-inuced Liver Injury (DILI):	0.278
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.958
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.406
Carcinogencity:	0.861
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC85047

Natural Product ID:	NPC85047
*Common Name:**	Dichrostachine B
IUPAC Name:	(4aR,8R,8aS)-8-[[(1R,3S,4aS,7S,8aS)-3,7-dihydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]methyl]-8a-(5,7-dihydroxy-4-oxochromen-2-yl)-3-methoxy-7-methyl-5,8-dihydro-4aH-naphthalene-1,4-dione
Synonyms:
Standard InCHIKey:	DYFMUBBDBHDXDV-QUUXZHRUSA-N
Standard InCHI:	InChI=1S/C36H42O9/c1-17-7-8-21-33(43)28(44-6)14-30(42)36(21,31-13-26(41)32-25(40)9-19(37)10-27(32)45-31)22(17)11-23-18(2)24(39)12-29-34(3,4)15-20(38)16-35(23,29)5/h7,9-10,13-14,20-24,29,37-40H,2,8,11-12,15-16H2,1,3-6H3/t20-,21-,22+,23-,24-,29-,35+,36-/m0/s1
SMILES:	CC1=CC[C@H]2C(=O)C(=CC(=O)[C@]2([C@@H]1C[C@H]1C(=C)[C@H](C[C@H]2C(C)(C)C[C@@H](C[C@]12C)O)O)c1cc(=O)c2c(cc(cc2o1)O)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077605
PubChem CID:	44557089
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO15669	Dichrostachys cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19761234]
NPO15669	Dichrostachys cinerea	Species	Fabaceae	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	1
Others	1

Activity Type	# Activity
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		IC50	=	40000.0	nM	PMID[508181]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	>	10.0	uM	PMID[508181]

☑ 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 NPC85047 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	456
0.1-0.2	1674
0.2-0.3	3291
0.3-0.4	7666
0.4-0.5	10681
0.5-0.6	5650
0.6-0.7	5653
0.7-0.8	6113
0.8-0.85	1422
0.85-0.9	73
0.9-0.95	7
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC17274
1.0	High Similarity	NPC120857
0.9873	High Similarity	NPC286074
0.9873	High Similarity	NPC20734
0.9873	High Similarity	NPC54903
0.9811	High Similarity	NPC193698
0.9744	High Similarity	NPC103816
0.9744	High Similarity	NPC61382
0.9689	High Similarity	NPC469393
0.962	High Similarity	NPC469395
0.9379	High Similarity	NPC469394
0.908	High Similarity	NPC316262
0.908	High Similarity	NPC314653
0.8976	High Similarity	NPC315306
0.8976	High Similarity	NPC313717
0.8957	High Similarity	NPC475106
0.8951	High Similarity	NPC472618
0.8931	High Similarity	NPC470353
0.8889	High Similarity	NPC472617
0.8882	High Similarity	NPC470354
0.8882	High Similarity	NPC192587
0.8882	High Similarity	NPC470352
0.8846	High Similarity	NPC472447
0.8846	High Similarity	NPC472446
0.8834	High Similarity	NPC195136
0.8834	High Similarity	NPC313368
0.8795	High Similarity	NPC476255
0.8782	High Similarity	NPC473812
0.8782	High Similarity	NPC473813
0.8773	High Similarity	NPC105584
0.8773	High Similarity	NPC15815
0.8773	High Similarity	NPC90497
0.8765	High Similarity	NPC54830
0.8765	High Similarity	NPC56049
0.8757	High Similarity	NPC471969
0.8757	High Similarity	NPC475080
0.8743	High Similarity	NPC223413
0.8743	High Similarity	NPC193222
0.8712	High Similarity	NPC474637
0.8712	High Similarity	NPC257166
0.8698	High Similarity	NPC476159
0.8698	High Similarity	NPC118128
0.8698	High Similarity	NPC477529
0.8696	High Similarity	NPC154683
0.8696	High Similarity	NPC40356
0.8683	High Similarity	NPC476056
0.8683	High Similarity	NPC125465
0.8683	High Similarity	NPC251336
0.8679	High Similarity	NPC470460
0.8675	High Similarity	NPC100849
0.8659	High Similarity	NPC51247
0.8659	High Similarity	NPC295090
0.8659	High Similarity	NPC125969
0.8655	High Similarity	NPC98943
0.8655	High Similarity	NPC469345
0.8647	High Similarity	NPC154986
0.8642	High Similarity	NPC155686
0.8642	High Similarity	NPC193200
0.8634	High Similarity	NPC178484
0.8634	High Similarity	NPC470675
0.8634	High Similarity	NPC305965
0.8634	High Similarity	NPC473131
0.8634	High Similarity	NPC46882
0.8634	High Similarity	NPC132990
0.8634	High Similarity	NPC470569
0.8631	High Similarity	NPC105414
0.8631	High Similarity	NPC470341
0.8631	High Similarity	NPC234497
0.8631	High Similarity	NPC472058
0.8631	High Similarity	NPC324522
0.8625	High Similarity	NPC470461
0.8623	High Similarity	NPC469664
0.8623	High Similarity	NPC472049
0.8614	High Similarity	NPC94796
0.8614	High Similarity	NPC473022
0.8606	High Similarity	NPC98023
0.8606	High Similarity	NPC475107
0.8606	High Similarity	NPC121647
0.8606	High Similarity	NPC226462
0.8606	High Similarity	NPC43490
0.8605	High Similarity	NPC476199
0.8605	High Similarity	NPC476210
0.8599	High Similarity	NPC204469
0.8598	High Similarity	NPC271741
0.8598	High Similarity	NPC281137
0.8598	High Similarity	NPC208258
0.8598	High Similarity	NPC272196
0.8598	High Similarity	NPC287789
0.8598	High Similarity	NPC282390
0.8598	High Similarity	NPC1796
0.8598	High Similarity	NPC201127
0.8596	High Similarity	NPC86809
0.8596	High Similarity	NPC232412
0.8596	High Similarity	NPC294149
0.8596	High Similarity	NPC475398
0.8596	High Similarity	NPC98667
0.8589	High Similarity	NPC79375
0.8589	High Similarity	NPC37253
0.8588	High Similarity	NPC169018
0.858	High Similarity	NPC473770
0.858	High Similarity	NPC473509
0.858	High Similarity	NPC475131
0.858	High Similarity	NPC470340
0.858	High Similarity	NPC43345
0.858	High Similarity	NPC102810
0.858	High Similarity	NPC63514
0.8571	High Similarity	NPC62444
0.8571	High Similarity	NPC197972
0.8571	High Similarity	NPC188403
0.8571	High Similarity	NPC61258
0.8571	High Similarity	NPC470568
0.8563	High Similarity	NPC476295
0.8563	High Similarity	NPC290160
0.8563	High Similarity	NPC131578
0.8555	High Similarity	NPC473729
0.8555	High Similarity	NPC473607
0.8554	High Similarity	NPC476929
0.8553	High Similarity	NPC470458
0.8547	High Similarity	NPC227275
0.8538	High Similarity	NPC470333
0.8538	High Similarity	NPC476311
0.8537	High Similarity	NPC469507
0.8537	High Similarity	NPC164427
0.8537	High Similarity	NPC32867
0.8537	High Similarity	NPC198489
0.8537	High Similarity	NPC309648
0.8537	High Similarity	NPC61112
0.8529	High Similarity	NPC476196
0.8528	High Similarity	NPC121568
0.8528	High Similarity	NPC214632
0.8528	High Similarity	NPC324447
0.8521	High Similarity	NPC470377
0.8521	High Similarity	NPC472622
0.8521	High Similarity	NPC471975
0.8521	High Similarity	NPC470374
0.8521	High Similarity	NPC76647
0.8521	High Similarity	NPC478059
0.8521	High Similarity	NPC478060
0.8519	High Similarity	NPC476551
0.8519	High Similarity	NPC476553
0.8519	High Similarity	NPC476552
0.8519	High Similarity	NPC478148
0.8512	High Similarity	NPC472051
0.8512	High Similarity	NPC472057
0.8509	High Similarity	NPC471114
0.8509	High Similarity	NPC146014
0.8506	High Similarity	NPC208069
0.8503	High Similarity	NPC472059
0.8503	High Similarity	NPC473012
0.85	High Similarity	NPC10990
0.85	High Similarity	NPC259632
0.85	High Similarity	NPC300988
0.8497	Intermediate Similarity	NPC233978
0.8497	Intermediate Similarity	NPC477683
0.8497	Intermediate Similarity	NPC477682
0.8494	Intermediate Similarity	NPC42965
0.8494	Intermediate Similarity	NPC286422
0.8491	Intermediate Similarity	NPC476055
0.8491	Intermediate Similarity	NPC470673
0.8491	Intermediate Similarity	NPC117716
0.8491	Intermediate Similarity	NPC224714
0.8491	Intermediate Similarity	NPC470674
0.8488	Intermediate Similarity	NPC477991
0.8488	Intermediate Similarity	NPC477992
0.8485	Intermediate Similarity	NPC475184
0.8481	Intermediate Similarity	NPC325346
0.8481	Intermediate Similarity	NPC277369
0.8481	Intermediate Similarity	NPC215451
0.848	Intermediate Similarity	NPC472620
0.8476	Intermediate Similarity	NPC258474
0.8476	Intermediate Similarity	NPC201227
0.8476	Intermediate Similarity	NPC304745
0.8476	Intermediate Similarity	NPC68727
0.8476	Intermediate Similarity	NPC111341
0.8471	Intermediate Similarity	NPC472619
0.8471	Intermediate Similarity	NPC41598
0.8471	Intermediate Similarity	NPC75141
0.8471	Intermediate Similarity	NPC476146
0.8471	Intermediate Similarity	NPC158329
0.8471	Intermediate Similarity	NPC47634
0.8471	Intermediate Similarity	NPC188079
0.8471	Intermediate Similarity	NPC40089
0.8471	Intermediate Similarity	NPC476216
0.8471	Intermediate Similarity	NPC55422
0.8466	Intermediate Similarity	NPC113608
0.8466	Intermediate Similarity	NPC180944
0.8466	Intermediate Similarity	NPC87708
0.8466	Intermediate Similarity	NPC268992
0.8466	Intermediate Similarity	NPC174086
0.8466	Intermediate Similarity	NPC470337
0.8466	Intermediate Similarity	NPC470338
0.8466	Intermediate Similarity	NPC51824
0.8462	Intermediate Similarity	NPC475109
0.8462	Intermediate Similarity	NPC25427
0.8462	Intermediate Similarity	NPC472621
0.8457	Intermediate Similarity	NPC29777
0.8457	Intermediate Similarity	NPC255641
0.8457	Intermediate Similarity	NPC290954
0.8457	Intermediate Similarity	NPC147735
0.8457	Intermediate Similarity	NPC471115

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 NPC85047 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	391
0.1-0.2	975
0.2-0.3	1793
0.3-0.4	2650
0.4-0.5	2038
0.5-0.6	866
0.6-0.7	282
0.7-0.8	140
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8589	High Similarity	NPD8443	Clinical (unspecified phase)
0.8375	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD7075	Discontinued
0.8363	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6959	Discontinued
0.8303	Intermediate Similarity	NPD7819	Suspended
0.8261	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD6801	Discontinued
0.8232	Intermediate Similarity	NPD4380	Phase 2
0.8193	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6166	Phase 2
0.8187	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6599	Discontinued
0.8113	Intermediate Similarity	NPD1549	Phase 2
0.8101	Intermediate Similarity	NPD2796	Approved
0.8081	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD7411	Suspended
0.8068	Intermediate Similarity	NPD7808	Phase 3
0.805	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.805	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD1510	Phase 2
0.8011	Intermediate Similarity	NPD7251	Discontinued
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD3882	Suspended
0.7988	Intermediate Similarity	NPD7768	Phase 2
0.7976	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7955	Intermediate Similarity	NPD6797	Phase 2
0.795	Intermediate Similarity	NPD2800	Approved
0.7939	Intermediate Similarity	NPD5403	Approved
0.7931	Intermediate Similarity	NPD7473	Discontinued
0.7929	Intermediate Similarity	NPD5402	Approved
0.7911	Intermediate Similarity	NPD6651	Approved
0.7901	Intermediate Similarity	NPD3750	Approved
0.7889	Intermediate Similarity	NPD8434	Phase 2
0.7888	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6100	Approved
0.7875	Intermediate Similarity	NPD6099	Approved
0.7866	Intermediate Similarity	NPD6799	Approved
0.7853	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7841	Intermediate Similarity	NPD7054	Approved
0.7824	Intermediate Similarity	NPD3817	Phase 2
0.7818	Intermediate Similarity	NPD5401	Approved
0.7811	Intermediate Similarity	NPD1934	Approved
0.7799	Intermediate Similarity	NPD1607	Approved
0.7797	Intermediate Similarity	NPD7472	Approved
0.7797	Intermediate Similarity	NPD7074	Phase 3
0.7791	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1240	Approved
0.7784	Intermediate Similarity	NPD3818	Discontinued
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1512	Approved
0.7765	Intermediate Similarity	NPD2801	Approved
0.7765	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD6232	Discontinued
0.7746	Intermediate Similarity	NPD5494	Approved
0.7733	Intermediate Similarity	NPD3749	Approved
0.7711	Intermediate Similarity	NPD2534	Approved
0.7711	Intermediate Similarity	NPD2532	Approved
0.7711	Intermediate Similarity	NPD2533	Approved
0.7702	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8150	Discontinued
0.7684	Intermediate Similarity	NPD3751	Discontinued
0.7651	Intermediate Similarity	NPD1511	Approved
0.7647	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5844	Phase 1
0.7633	Intermediate Similarity	NPD3226	Approved
0.7624	Intermediate Similarity	NPD8312	Approved
0.7624	Intermediate Similarity	NPD8313	Approved
0.7593	Intermediate Similarity	NPD3748	Approved
0.7576	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD4628	Phase 3
0.7558	Intermediate Similarity	NPD5761	Phase 2
0.7558	Intermediate Similarity	NPD5760	Phase 2
0.7545	Intermediate Similarity	NPD7390	Discontinued
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD6559	Discontinued
0.7514	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7698	Approved
0.75	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7696	Phase 3
0.75	Intermediate Similarity	NPD7697	Approved
0.75	Intermediate Similarity	NPD7435	Discontinued
0.7486	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7870	Phase 2
0.7461	Intermediate Similarity	NPD7871	Phase 2
0.7459	Intermediate Similarity	NPD5953	Discontinued
0.7439	Intermediate Similarity	NPD1551	Phase 2
0.7438	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD6782	Approved
0.7435	Intermediate Similarity	NPD6779	Approved
0.7435	Intermediate Similarity	NPD6780	Approved
0.7435	Intermediate Similarity	NPD6781	Approved
0.7435	Intermediate Similarity	NPD6776	Approved
0.7435	Intermediate Similarity	NPD6777	Approved
0.7435	Intermediate Similarity	NPD6778	Approved
0.7427	Intermediate Similarity	NPD7458	Discontinued
0.7416	Intermediate Similarity	NPD3926	Phase 2
0.7398	Intermediate Similarity	NPD8151	Discontinued
0.7394	Intermediate Similarity	NPD2344	Approved
0.7378	Intermediate Similarity	NPD2799	Discontinued
0.736	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD7874	Approved
0.736	Intermediate Similarity	NPD3787	Discontinued
0.7353	Intermediate Similarity	NPD6273	Approved
0.7351	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7701	Phase 2
0.7329	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD7801	Approved
0.7312	Intermediate Similarity	NPD4908	Phase 1
0.731	Intermediate Similarity	NPD920	Approved
0.7305	Intermediate Similarity	NPD1243	Approved
0.7303	Intermediate Similarity	NPD1247	Approved
0.7289	Intermediate Similarity	NPD1471	Phase 3
0.7288	Intermediate Similarity	NPD919	Approved
0.7282	Intermediate Similarity	NPD8320	Phase 1
0.7282	Intermediate Similarity	NPD8319	Approved
0.7263	Intermediate Similarity	NPD4360	Phase 2
0.7263	Intermediate Similarity	NPD4363	Phase 3
0.7262	Intermediate Similarity	NPD7003	Approved
0.7257	Intermediate Similarity	NPD1465	Phase 2
0.7253	Intermediate Similarity	NPD7286	Phase 2
0.724	Intermediate Similarity	NPD7699	Phase 2
0.724	Intermediate Similarity	NPD7700	Phase 2
0.7229	Intermediate Similarity	NPD2935	Discontinued
0.7219	Intermediate Similarity	NPD2309	Approved
0.7207	Intermediate Similarity	NPD8127	Discontinued
0.72	Intermediate Similarity	NPD37	Approved
0.7198	Intermediate Similarity	NPD7228	Approved
0.7193	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD2346	Discontinued
0.7182	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7236	Approved
0.7176	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4967	Phase 2
0.7175	Intermediate Similarity	NPD4966	Approved
0.7175	Intermediate Similarity	NPD4965	Approved
0.7173	Intermediate Similarity	NPD6534	Approved
0.7173	Intermediate Similarity	NPD6535	Approved
0.7167	Intermediate Similarity	NPD5710	Approved
0.7167	Intermediate Similarity	NPD5711	Approved
0.716	Intermediate Similarity	NPD8166	Discontinued
0.7127	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1470	Approved
0.7117	Intermediate Similarity	NPD2313	Discontinued
0.7099	Intermediate Similarity	NPD6832	Phase 2
0.7095	Intermediate Similarity	NPD6234	Discontinued
0.7091	Intermediate Similarity	NPD5124	Phase 1
0.7091	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD2403	Approved
0.7081	Intermediate Similarity	NPD2798	Approved
0.7077	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7229	Phase 3
0.7069	Intermediate Similarity	NPD7239	Suspended
0.7066	Intermediate Similarity	NPD7033	Discontinued
0.7065	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7783	Phase 2
0.7047	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4361	Phase 2
0.703	Intermediate Similarity	NPD943	Approved
0.7022	Intermediate Similarity	NPD4288	Approved
0.7017	Intermediate Similarity	NPD7199	Phase 2
0.7012	Intermediate Similarity	NPD3268	Approved
0.7011	Intermediate Similarity	NPD7799	Discontinued
0.7011	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6844	Discontinued
0.7005	Intermediate Similarity	NPD7907	Approved
0.7005	Intermediate Similarity	NPD6823	Phase 2
0.7005	Intermediate Similarity	NPD8366	Approved
0.7005	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4749	Approved
0.6988	Remote Similarity	NPD6355	Discontinued
0.6981	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1610	Phase 2
0.6966	Remote Similarity	NPD8455	Phase 2
0.6964	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6765	Approved
0.6952	Remote Similarity	NPD6764	Approved
0.695	Remote Similarity	NPD7584	Approved
0.6949	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD8285	Discontinued
0.6937	Remote Similarity	NPD3972	Approved
0.6923	Remote Similarity	NPD5408	Approved
0.6923	Remote Similarity	NPD5404	Approved
0.6923	Remote Similarity	NPD5406	Approved
0.6923	Remote Similarity	NPD5405	Approved
0.6919	Remote Similarity	NPD6190	Approved
0.6914	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD2797	Approved
0.6914	Remote Similarity	NPD1203	Approved
0.6909	Remote Similarity	NPD6798	Discontinued
0.6897	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD8404	Phase 2
0.6886	Remote Similarity	NPD230	Phase 1
0.6875	Remote Similarity	NPD1201	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