NPASS Compound

Structure

CID108674 OpenBabel06191715462D 31 35 0 0 1 0 0 0 0 0999 V2000 9.9344 2.1798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4575 2.9089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4559 0.0227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6244 3.3902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2893 0.5036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6240 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6230 1.4662 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7484 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2899 3.3908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4573 1.9461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6228 0.5040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7905 2.9092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2896 1.4658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1236 2.9095 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4564 1.9471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7903 1.9464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8741 0.5050 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8738 1.5144 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0005 2.0189 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8746 1.5140 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1234 1.9467 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8743 0.5045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6225 0.5054 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7479 2.0194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0008 3.0284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7490 2.0185 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2905 1.4649 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4566 2.9098 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7484 -0.0005 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9570 1.4654 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 27 1 0 0 0 0 2 4 2 0 0 0 0 2 10 1 0 0 0 0 3 5 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 13 1 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 23 1 0 0 0 0 9 28 1 0 0 0 0 10 27 1 0 0 0 0 11 29 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 15 2 0 0 0 0 14 9 1 1 0 0 0 14 21 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 8 1 6 0 0 0 17 18 1 0 0 0 0 17 31 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 1 0 0 0 19 20 1 0 0 0 0 19 25 1 6 0 0 0 20 22 1 0 0 0 0 20 26 1 1 0 0 0 21 13 1 1 0 0 0 21 30 1 0 0 0 0 22 29 1 6 0 0 0 22 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.14
Volume:	409.579
LogP:	1.35
LogD:	1.712
LogS:	-4.168
# Rotatable Bonds:	4
TPSA:	127.07
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.546
Synthetic Accessibility Score:	4.111
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.172
MDCK Permeability:	2.6858628189074807e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.267
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.102

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	93.35426330566406%
Volume Distribution (VD):	0.707
Pgp-substrate:	5.382194519042969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.075
CYP1A2-substrate:	0.502
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.803
CYP2C9-inhibitor:	0.092
CYP2C9-substrate:	0.688
CYP2D6-inhibitor:	0.112
CYP2D6-substrate:	0.838
CYP3A4-inhibitor:	0.134
CYP3A4-substrate:	0.493

ADMET: Excretion

Clearance (CL):	3.305
Half-life (T1/2):	0.186

ADMET: Toxicity

hERG Blockers:	0.293
Human Hepatotoxicity (H-HT):	0.74
Drug-inuced Liver Injury (DILI):	0.726
AMES Toxicity:	0.874
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.129
Skin Sensitization:	0.437
Carcinogencity:	0.719
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.108

Download Data

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

Natural Product: NPC108674

Natural Product ID:	NPC108674
*Common Name:**	7-Demethoxy-7-D-(Glucosyloxy)-Homopterocarpin
IUPAC Name:	(2S,3R,4S,5S,6R)-2-[[(6aR,11aR)-9-methoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:
Standard InCHIKey:	PVEMGMOWXQUWRD-NJAOXFEXSA-N
Standard InCHI:	InChI=1S/C22H24O9/c1-27-10-2-4-12-14-9-28-15-7-11(3-5-13(15)21(14)30-16(12)6-10)29-22-20(26)19(25)18(24)17(8-23)31-22/h2-7,14,17-26H,8-9H2,1H3/t14-,17+,18+,19-,20+,21-,22+/m0/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc3c(c2)OC[C@@H]2[C@H]3Oc3c2ccc(c3)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517330
PubChem CID:	23724664
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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
NPO20620	Eucalyptus cypellocarpa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000030]
NPO6731.1	Ononis spinosa	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9182126]
NPO17542	Aconitum orientale	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17315	Ceanothus integerrimus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17315	Ceanothus integerrimus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20620	Eucalyptus cypellocarpa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17542	Aconitum orientale	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12227	Xylopia acutiflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24375	Micrococcus luteus	Species	Micrococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23977	Helichrysum moeserianum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15338	Lampranthus aurantiacus	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18125	Suillus variegatus	Species	Suillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20277	Pentzia eenii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25819.1	Gueldenstaedtia verna subsp. multiflora	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19504	Solanum canense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20346	Acacia retinoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18462	Calliactis parasitica	Species	Hormathiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20620	Eucalyptus cypellocarpa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17315	Ceanothus integerrimus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17542	Aconitum orientale	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19033	Sargassum lacerifolium	Species	Sargassaceae	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	200.0	ug.mL-1	PMID[510272]

☑ 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 NPC108674 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	381
0.1-0.2	1398
0.2-0.3	3362
0.3-0.4	8993
0.4-0.5	9564
0.5-0.6	5137
0.6-0.7	8046
0.7-0.8	4731
0.8-0.85	828
0.85-0.9	221
0.9-0.95	33
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9632	High Similarity	NPC472353
0.9481	High Similarity	NPC87777
0.9481	High Similarity	NPC262328
0.9231	High Similarity	NPC238140
0.9225	High Similarity	NPC270751
0.9209	High Similarity	NPC49542
0.9209	High Similarity	NPC5253
0.9209	High Similarity	NPC84207
0.9209	High Similarity	NPC139976
0.9209	High Similarity	NPC128337
0.9209	High Similarity	NPC230718
0.9143	High Similarity	NPC116922
0.9137	High Similarity	NPC5155
0.9137	High Similarity	NPC210192
0.913	High Similarity	NPC475836
0.9085	High Similarity	NPC125755
0.9078	High Similarity	NPC225445
0.9078	High Similarity	NPC138227
0.9078	High Similarity	NPC76176
0.9078	High Similarity	NPC469313
0.9078	High Similarity	NPC177597
0.9078	High Similarity	NPC168579
0.9051	High Similarity	NPC238243
0.9044	High Similarity	NPC215037
0.9028	High Similarity	NPC55715
0.9028	High Similarity	NPC35877
0.9028	High Similarity	NPC95392
0.9021	High Similarity	NPC473480
0.9021	High Similarity	NPC15538
0.9021	High Similarity	NPC39657
0.9014	High Similarity	NPC277867
0.9014	High Similarity	NPC161700
0.9007	High Similarity	NPC37793
0.8986	High Similarity	NPC197723
0.8986	High Similarity	NPC138350
0.8986	High Similarity	NPC40664
0.8986	High Similarity	NPC165482
0.8986	High Similarity	NPC3293
0.8978	High Similarity	NPC130496
0.8978	High Similarity	NPC188555
0.8973	High Similarity	NPC59692
0.8973	High Similarity	NPC302610
0.8973	High Similarity	NPC233467
0.8966	High Similarity	NPC472710
0.8966	High Similarity	NPC472709
0.8963	High Similarity	NPC474491
0.8951	High Similarity	NPC248053
0.8951	High Similarity	NPC99515
0.8951	High Similarity	NPC107120
0.8951	High Similarity	NPC190714
0.8951	High Similarity	NPC155564
0.8951	High Similarity	NPC102280
0.8951	High Similarity	NPC74320
0.8944	High Similarity	NPC471667
0.8944	High Similarity	NPC79429
0.8944	High Similarity	NPC217635
0.8944	High Similarity	NPC471063
0.8921	High Similarity	NPC134260
0.8913	High Similarity	NPC79957
0.8905	High Similarity	NPC294166
0.8905	High Similarity	NPC115022
0.8904	High Similarity	NPC259707
0.8897	High Similarity	NPC162801
0.8897	High Similarity	NPC286235
0.8897	High Similarity	NPC475067
0.8897	High Similarity	NPC51328
0.8897	High Similarity	NPC55158
0.8881	High Similarity	NPC476301
0.8881	High Similarity	NPC226722
0.8881	High Similarity	NPC475096
0.8881	High Similarity	NPC43508
0.8873	High Similarity	NPC473044
0.8849	High Similarity	NPC18189
0.8849	High Similarity	NPC262585
0.8849	High Similarity	NPC20829
0.8841	High Similarity	NPC117048
0.8841	High Similarity	NPC124085
0.8832	High Similarity	NPC303422
0.8832	High Similarity	NPC165686
0.8832	High Similarity	NPC85799
0.8832	High Similarity	NPC26080
0.8828	High Similarity	NPC248132
0.8828	High Similarity	NPC130449
0.8828	High Similarity	NPC280945
0.8828	High Similarity	NPC175976
0.8819	High Similarity	NPC276753
0.8819	High Similarity	NPC205796
0.8815	High Similarity	NPC47283
0.8815	High Similarity	NPC39064
0.8811	High Similarity	NPC473046
0.8811	High Similarity	NPC473045
0.8811	High Similarity	NPC472712
0.8811	High Similarity	NPC187774
0.8811	High Similarity	NPC472713
0.8811	High Similarity	NPC25292
0.8811	High Similarity	NPC118385
0.8803	High Similarity	NPC246947
0.8803	High Similarity	NPC475084
0.8803	High Similarity	NPC189115
0.8797	High Similarity	NPC256015
0.8797	High Similarity	NPC294156
0.8794	High Similarity	NPC226547
0.8786	High Similarity	NPC474687
0.8776	High Similarity	NPC473621
0.8768	High Similarity	NPC85435
0.8759	High Similarity	NPC193473
0.8759	High Similarity	NPC207892
0.8759	High Similarity	NPC87950
0.8759	High Similarity	NPC236014
0.8759	High Similarity	NPC164574
0.8759	High Similarity	NPC213074
0.8759	High Similarity	NPC300875
0.8759	High Similarity	NPC227902
0.8759	High Similarity	NPC196765
0.8759	High Similarity	NPC129784
0.8759	High Similarity	NPC103799
0.8759	High Similarity	NPC15956
0.8759	High Similarity	NPC296377
0.8759	High Similarity	NPC121376
0.8759	High Similarity	NPC228369
0.8759	High Similarity	NPC118114
0.8759	High Similarity	NPC476166
0.8759	High Similarity	NPC471764
0.8759	High Similarity	NPC12875
0.8759	High Similarity	NPC224674
0.8759	High Similarity	NPC206224
0.8759	High Similarity	NPC17343
0.8759	High Similarity	NPC31325
0.8759	High Similarity	NPC129106
0.8759	High Similarity	NPC114505
0.8759	High Similarity	NPC275284
0.8759	High Similarity	NPC268917
0.8759	High Similarity	NPC150011
0.8759	High Similarity	NPC280653
0.875	High Similarity	NPC307466
0.8741	High Similarity	NPC81638
0.8741	High Similarity	NPC185307
0.8741	High Similarity	NPC470950
0.8732	High Similarity	NPC277331
0.8732	High Similarity	NPC469661
0.8732	High Similarity	NPC273932
0.8732	High Similarity	NPC257095
0.8732	High Similarity	NPC89686
0.8732	High Similarity	NPC100482
0.8723	High Similarity	NPC183781
0.8723	High Similarity	NPC292487
0.8716	High Similarity	NPC21902
0.8714	High Similarity	NPC469383
0.8714	High Similarity	NPC25695
0.8714	High Similarity	NPC172818
0.8714	High Similarity	NPC3049
0.8705	High Similarity	NPC225696
0.8705	High Similarity	NPC198154
0.8705	High Similarity	NPC296915
0.8705	High Similarity	NPC97834
0.8705	High Similarity	NPC115335
0.8705	High Similarity	NPC223008
0.8699	High Similarity	NPC169510
0.8699	High Similarity	NPC166584
0.8699	High Similarity	NPC301961
0.8696	High Similarity	NPC13005
0.869	High Similarity	NPC162193
0.8686	High Similarity	NPC27187
0.8686	High Similarity	NPC470225
0.8681	High Similarity	NPC129417
0.8681	High Similarity	NPC470235
0.8681	High Similarity	NPC283995
0.8676	High Similarity	NPC87224
0.8676	High Similarity	NPC222572
0.8671	High Similarity	NPC476356
0.8671	High Similarity	NPC469559
0.8671	High Similarity	NPC472714
0.8671	High Similarity	NPC80326
0.8671	High Similarity	NPC5262
0.8667	High Similarity	NPC50315
0.8667	High Similarity	NPC283049
0.8667	High Similarity	NPC471215
0.8667	High Similarity	NPC262573
0.8667	High Similarity	NPC230479
0.8667	High Similarity	NPC26879
0.8662	High Similarity	NPC184797
0.8662	High Similarity	NPC309124
0.8658	High Similarity	NPC78809
0.8657	High Similarity	NPC287429
0.8652	High Similarity	NPC283949
0.8652	High Similarity	NPC185908
0.8652	High Similarity	NPC124149
0.8649	High Similarity	NPC471403
0.8647	High Similarity	NPC476142
0.8643	High Similarity	NPC236522
0.8643	High Similarity	NPC470236
0.8633	High Similarity	NPC92805
0.8633	High Similarity	NPC215833
0.8633	High Similarity	NPC69513
0.8633	High Similarity	NPC196937
0.8633	High Similarity	NPC263064
0.8623	High Similarity	NPC181497
0.8623	High Similarity	NPC271945
0.8621	High Similarity	NPC22150
0.8621	High Similarity	NPC180953

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 NPC108674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	299
0.1-0.2	806
0.2-0.3	1676
0.3-0.4	2769
0.4-0.5	1803
0.5-0.6	1067
0.6-0.7	605
0.7-0.8	115
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.854	High Similarity	NPD4908	Phase 1
0.8433	Intermediate Similarity	NPD1091	Approved
0.8417	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD1613	Approved
0.8298	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD1610	Phase 2
0.8194	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD8455	Phase 2
0.8095	Intermediate Similarity	NPD6674	Discontinued
0.8054	Intermediate Similarity	NPD5058	Phase 3
0.8038	Intermediate Similarity	NPD7199	Phase 2
0.8014	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7228	Approved
0.7963	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD3027	Phase 3
0.7943	Intermediate Similarity	NPD2861	Phase 2
0.7943	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD37	Approved
0.7914	Intermediate Similarity	NPD7074	Phase 3
0.7908	Intermediate Similarity	NPD1653	Approved
0.7898	Intermediate Similarity	NPD4966	Approved
0.7898	Intermediate Similarity	NPD4967	Phase 2
0.7898	Intermediate Similarity	NPD4965	Approved
0.7868	Intermediate Similarity	NPD1548	Phase 1
0.7853	Intermediate Similarity	NPD7054	Approved
0.7826	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7240	Approved
0.7818	Intermediate Similarity	NPD6559	Discontinued
0.7805	Intermediate Similarity	NPD7472	Approved
0.7799	Intermediate Similarity	NPD6234	Discontinued
0.7791	Intermediate Similarity	NPD3818	Discontinued
0.7758	Intermediate Similarity	NPD6797	Phase 2
0.774	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD5124	Phase 1
0.7733	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1652	Phase 2
0.7718	Intermediate Similarity	NPD7266	Discontinued
0.7711	Intermediate Similarity	NPD7251	Discontinued
0.7703	Intermediate Similarity	NPD5588	Approved
0.7665	Intermediate Similarity	NPD7808	Phase 3
0.766	Intermediate Similarity	NPD4749	Approved
0.7655	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7655	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7157	Approved
0.7635	Intermediate Similarity	NPD4538	Approved
0.7635	Intermediate Similarity	NPD7097	Phase 1
0.7635	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD4536	Approved
0.7626	Intermediate Similarity	NPD5125	Phase 3
0.7626	Intermediate Similarity	NPD5126	Approved
0.7619	Intermediate Similarity	NPD6355	Discontinued
0.7606	Intermediate Similarity	NPD8651	Approved
0.7586	Intermediate Similarity	NPD4625	Phase 3
0.758	Intermediate Similarity	NPD4380	Phase 2
0.7566	Intermediate Similarity	NPD7466	Approved
0.7556	Intermediate Similarity	NPD7843	Approved
0.7519	Intermediate Similarity	NPD2684	Approved
0.7518	Intermediate Similarity	NPD3705	Approved
0.7467	Intermediate Similarity	NPD5960	Phase 3
0.7456	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6166	Phase 2
0.7455	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD290	Approved
0.7439	Intermediate Similarity	NPD3787	Discontinued
0.7438	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4060	Phase 1
0.7423	Intermediate Similarity	NPD5494	Approved
0.7419	Intermediate Similarity	NPD7212	Phase 2
0.7419	Intermediate Similarity	NPD7213	Phase 3
0.7415	Intermediate Similarity	NPD6798	Discontinued
0.7407	Intermediate Similarity	NPD7075	Discontinued
0.7391	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1934	Approved
0.7372	Intermediate Similarity	NPD7447	Phase 1
0.7372	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5762	Approved
0.7368	Intermediate Similarity	NPD5763	Approved
0.7338	Intermediate Similarity	NPD3892	Phase 2
0.7329	Intermediate Similarity	NPD3018	Phase 2
0.7329	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD2424	Discontinued
0.7312	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5403	Approved
0.7273	Intermediate Similarity	NPD422	Phase 1
0.7267	Intermediate Similarity	NPD6801	Discontinued
0.7267	Intermediate Similarity	NPD5735	Approved
0.7261	Intermediate Similarity	NPD5401	Approved
0.726	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6516	Phase 2
0.7254	Intermediate Similarity	NPD5846	Approved
0.7248	Intermediate Similarity	NPD6233	Phase 2
0.7237	Intermediate Similarity	NPD4108	Discontinued
0.7237	Intermediate Similarity	NPD7033	Discontinued
0.7226	Intermediate Similarity	NPD3750	Approved
0.7226	Intermediate Similarity	NPD4628	Phase 3
0.7222	Intermediate Similarity	NPD7819	Suspended
0.7219	Intermediate Similarity	NPD5844	Phase 1
0.7209	Intermediate Similarity	NPD8313	Approved
0.7209	Intermediate Similarity	NPD8312	Approved
0.7208	Intermediate Similarity	NPD1549	Phase 2
0.7205	Intermediate Similarity	NPD7411	Suspended
0.7197	Intermediate Similarity	NPD6799	Approved
0.719	Intermediate Similarity	NPD2796	Approved
0.7183	Intermediate Similarity	NPD1357	Approved
0.7178	Intermediate Similarity	NPD5402	Approved
0.7178	Intermediate Similarity	NPD3817	Phase 2
0.7172	Intermediate Similarity	NPD2982	Phase 2
0.7172	Intermediate Similarity	NPD2983	Phase 2
0.7172	Intermediate Similarity	NPD3685	Discontinued
0.7171	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD3384	Approved
0.716	Intermediate Similarity	NPD3751	Discontinued
0.716	Intermediate Similarity	NPD3382	Approved
0.716	Intermediate Similarity	NPD3383	Approved
0.7152	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6005	Phase 3
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.7143	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6004	Phase 3
0.7143	Intermediate Similarity	NPD6002	Phase 3
0.7143	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7229	Phase 3
0.7124	Intermediate Similarity	NPD3748	Approved
0.7122	Intermediate Similarity	NPD5283	Phase 1
0.7115	Intermediate Similarity	NPD4535	Phase 3
0.7114	Intermediate Similarity	NPD7095	Approved
0.7104	Intermediate Similarity	NPD7680	Approved
0.7103	Intermediate Similarity	NPD2981	Phase 2
0.7089	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4140	Approved
0.7086	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6100	Approved
0.7078	Intermediate Similarity	NPD6099	Approved
0.7075	Intermediate Similarity	NPD2797	Approved
0.7073	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD2677	Approved
0.7066	Intermediate Similarity	NPD6959	Discontinued
0.7059	Intermediate Similarity	NPD2200	Suspended
0.7059	Intermediate Similarity	NPD7119	Phase 2
0.7051	Intermediate Similarity	NPD5061	Approved
0.7051	Intermediate Similarity	NPD5062	Approved
0.705	Intermediate Similarity	NPD5535	Approved
0.7045	Intermediate Similarity	NPD6842	Approved
0.7045	Intermediate Similarity	NPD6843	Phase 3
0.7045	Intermediate Similarity	NPD6841	Approved
0.703	Intermediate Similarity	NPD7768	Phase 2
0.703	Intermediate Similarity	NPD3882	Suspended
0.7029	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3122	Phase 3
0.7021	Intermediate Similarity	NPD6671	Approved
0.7013	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2801	Approved
0.7012	Intermediate Similarity	NPD1465	Phase 2
0.7006	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7685	Pre-registration
0.6993	Remote Similarity	NPD6653	Approved
0.6975	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD2238	Phase 2
0.6954	Remote Similarity	NPD3268	Approved
0.6954	Remote Similarity	NPD7549	Discontinued
0.6941	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5327	Phase 3
0.6939	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7007	Discovery
0.6928	Remote Similarity	NPD4340	Discontinued
0.6927	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3051	Approved
0.6923	Remote Similarity	NPD1375	Discontinued
0.6918	Remote Similarity	NPD6666	Approved
0.6918	Remote Similarity	NPD6667	Approved
0.6908	Remote Similarity	NPD4062	Phase 3
0.6903	Remote Similarity	NPD1510	Phase 2
0.6894	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3225	Approved
0.689	Remote Similarity	NPD6072	Discontinued
0.6886	Remote Similarity	NPD3749	Approved
0.6882	Remote Similarity	NPD2969	Approved
0.6882	Remote Similarity	NPD2970	Approved
0.6879	Remote Similarity	NPD5958	Discontinued
0.6875	Remote Similarity	NPD1511	Approved
0.6871	Remote Similarity	NPD7458	Discontinued
0.6871	Remote Similarity	NPD1608	Approved
0.6864	Remote Similarity	NPD8127	Discontinued
0.6863	Remote Similarity	NPD3620	Phase 2
0.6863	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD3597	Clinical (unspecified phase)
0.6861	Remote Similarity	NPD968	Approved
0.6859	Remote Similarity	NPD6032	Approved
0.6855	Remote Similarity	NPD5307	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