NPASS Compound

Structure

NPC43716 OpenBabel07101719252D 38 43 0 0 1 0 0 0 0 0999 V2000 -0.8095 -4.2065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4764 -1.8696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8095 2.3370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2382 -1.8696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6668 1.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2382 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8573 0.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4286 -0.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0477 -1.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6191 -2.8043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.8043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6191 -1.8696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4764 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4286 1.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6191 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8095 -3.2717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4286 -1.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4764 0.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2382 0.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8573 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6191 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8095 -1.4022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6191 -1.8696 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.8696 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4286 -0.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6668 -0.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6191 0.9348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8095 -0.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0477 -0.4674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8095 -1.4022 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8095 -0.4674 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2859 1.4022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0477 1.4022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8573 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6668 -1.4022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8095 1.4022 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2382 -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 16 1 0 0 0 0 2 35 1 0 0 0 0 3 36 1 0 0 0 0 4 9 2 0 0 0 0 4 17 1 0 0 0 0 5 7 2 0 0 0 0 5 18 1 0 0 0 0 6 8 2 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 21 1 0 0 0 0 9 29 1 0 0 0 0 10 16 1 0 0 0 0 10 23 1 0 0 0 0 11 16 2 0 0 0 0 12 17 2 0 0 0 0 12 22 1 0 0 0 0 13 18 2 0 0 0 0 13 26 1 0 0 0 0 14 19 2 0 0 0 0 14 27 1 0 0 0 0 15 25 2 0 0 0 0 15 28 1 0 0 0 0 17 25 1 0 0 0 0 18 32 1 0 0 0 0 19 33 1 0 0 0 0 20 26 2 0 0 0 0 21 27 2 0 0 0 0 21 31 1 0 0 0 0 22 24 1 0 0 0 0 22 28 2 0 0 0 0 23 20 1 1 0 0 0 23 30 1 0 0 0 0 24 11 1 6 0 0 0 24 30 1 0 0 0 0 25 37 1 0 0 0 0 26 35 1 0 0 0 0 27 36 1 0 0 0 0 28 38 1 0 0 0 0 29 34 2 0 0 0 0 29 37 1 0 0 0 0 30 31 1 0 0 0 0 31 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.18
Volume:	523.287
LogP:	5.113
LogD:	4.074
LogS:	-4.153
# Rotatable Bonds:	4
TPSA:	98.36
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.249
Synthetic Accessibility Score:	4.2
Fsp3:	0.258
Lipinski Rule-of-5:	Rejected
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:	-5.03
MDCK Permeability:	3.2681342418072745e-05
Pgp-inhibitor:	0.078
Pgp-substrate:	0.971
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	94.02098083496094%
Volume Distribution (VD):	0.566
Pgp-substrate:	8.574644088745117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.274
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.964
CYP2C19-substrate:	0.201
CYP2C9-inhibitor:	0.941
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.648
CYP2D6-substrate:	0.92
CYP3A4-inhibitor:	0.878
CYP3A4-substrate:	0.792

ADMET: Excretion

Clearance (CL):	9.298
Half-life (T1/2):	0.343

ADMET: Toxicity

hERG Blockers:	0.222
Human Hepatotoxicity (H-HT):	0.378
Drug-inuced Liver Injury (DILI):	0.941
AMES Toxicity:	0.343
Rat Oral Acute Toxicity:	0.281
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.088
Carcinogencity:	0.085
Eye Corrosion:	0.003
Eye Irritation:	0.084
Respiratory Toxicity:	0.756

Download Data

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

Natural Product: NPC43716

Natural Product ID:	NPC43716
*Common Name:**	Palodesangren E
IUPAC Name:	(4R,4aS,5S,12bR)-4,5-bis(4-hydroxy-2-methoxyphenyl)-2-methyl-4,4a,5,12b-tetrahydro-3H-isochromeno[4,3-g]chromen-9-one
Synonyms:	Palodesangren E
Standard InCHIKey:	BKCPZBIJQGQCCP-ODJQGHGISA-N
Standard InCHI:	InChI=1S/C31H28O7/c1-16-10-23(20-7-5-18(32)13-26(20)35-2)30-24(11-16)22-12-17-4-9-29(34)37-25(17)15-28(22)38-31(30)21-8-6-19(33)14-27(21)36-3/h4-9,11-15,23-24,30-33H,10H2,1-3H3/t23-,24-,30-,31+/m0/s1
SMILES:	CC1=C[C@H]2c3cc4ccc(=O)oc4cc3O[C@H](c3ccc(cc3OC)O)[C@H]2[C@@H](C1)c1ccc(cc1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL466573
PubChem CID:	10255841
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0000337] Flavans [CHEMONTID:0003639] 3-prenylated flavans

*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
NPO5702	Brosimum rubescens	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9358642]
NPO5702	Brosimum rubescens	Species	Moraceae	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
Others	6

Activity Type	# Activity
Individual Protein	3
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT299	Individual Protein	Androgen Receptor	Rattus norvegicus	Inhibition	=	70.9	%	PMID[513105]
NPT299	Individual Protein	Androgen Receptor	Rattus norvegicus	Inhibition	=	60.3	%	PMID[513105]
NPT299	Individual Protein	Androgen Receptor	Rattus norvegicus	Inhibition	=	62.0	%	PMID[513105]
NPT2	Others	Unspecified		Inhibition	=	8.6	%	PMID[513105]
NPT2	Others	Unspecified		Inhibition	=	49.9	%	PMID[513105]
NPT2	Others	Unspecified		Inhibition	=	72.3	%	PMID[513105]

☑ 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 NPC43716 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	375
0.1-0.2	1595
0.2-0.3	3546
0.3-0.4	8162
0.4-0.5	10620
0.5-0.6	3957
0.6-0.7	5885
0.7-0.8	5121
0.8-0.85	2239
0.85-0.9	1015
0.9-0.95	178
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC101255
1.0	High Similarity	NPC475719
0.9448	High Similarity	NPC223720
0.9384	High Similarity	NPC268484
0.9143	High Similarity	NPC278600
0.9143	High Similarity	NPC35501
0.9143	High Similarity	NPC37428
0.9143	High Similarity	NPC47040
0.9143	High Similarity	NPC144512
0.9143	High Similarity	NPC137262
0.913	High Similarity	NPC131950
0.9085	High Similarity	NPC93640
0.9085	High Similarity	NPC20631
0.9014	High Similarity	NPC138149
0.8978	High Similarity	NPC32463
0.8921	High Similarity	NPC469952
0.8921	High Similarity	NPC31849
0.8921	High Similarity	NPC469955
0.8897	High Similarity	NPC108994
0.8897	High Similarity	NPC106126
0.8897	High Similarity	NPC469701
0.8873	High Similarity	NPC279573
0.8865	High Similarity	NPC471522
0.8849	High Similarity	NPC194277
0.8828	High Similarity	NPC471824
0.8803	High Similarity	NPC470308
0.8803	High Similarity	NPC306365
0.8803	High Similarity	NPC470307
0.8803	High Similarity	NPC131198
0.8786	High Similarity	NPC163557
0.8786	High Similarity	NPC141822
0.8786	High Similarity	NPC142563
0.8786	High Similarity	NPC77196
0.8786	High Similarity	NPC291551
0.8786	High Similarity	NPC1220
0.8786	High Similarity	NPC469965
0.8786	High Similarity	NPC241165
0.8786	High Similarity	NPC205797
0.8777	High Similarity	NPC293203
0.8777	High Similarity	NPC211413
0.8777	High Similarity	NPC244888
0.8777	High Similarity	NPC68205
0.8777	High Similarity	NPC118683
0.8777	High Similarity	NPC164804
0.8767	High Similarity	NPC295696
0.8759	High Similarity	NPC243688
0.875	High Similarity	NPC287286
0.875	High Similarity	NPC195357
0.875	High Similarity	NPC152771
0.8741	High Similarity	NPC211110
0.8732	High Similarity	NPC26954
0.8732	High Similarity	NPC38099
0.8723	High Similarity	NPC50896
0.8723	High Similarity	NPC184677
0.8723	High Similarity	NPC476616
0.8723	High Similarity	NPC296915
0.8723	High Similarity	NPC326600
0.8723	High Similarity	NPC97834
0.8723	High Similarity	NPC223008
0.8723	High Similarity	NPC204353
0.8723	High Similarity	NPC115335
0.8723	High Similarity	NPC225696
0.8723	High Similarity	NPC198154
0.8723	High Similarity	NPC476615
0.8723	High Similarity	NPC476617
0.8716	High Similarity	NPC142863
0.8714	High Similarity	NPC469956
0.8714	High Similarity	NPC19157
0.8699	High Similarity	NPC36732
0.8696	High Similarity	NPC38664
0.8696	High Similarity	NPC185066
0.8696	High Similarity	NPC53986
0.8681	High Similarity	NPC312881
0.8671	High Similarity	NPC153818
0.8671	High Similarity	NPC184861
0.8671	High Similarity	NPC294456
0.8671	High Similarity	NPC232246
0.8671	High Similarity	NPC212124
0.8671	High Similarity	NPC225106
0.8671	High Similarity	NPC281014
0.8662	High Similarity	NPC472424
0.8662	High Similarity	NPC471625
0.8662	High Similarity	NPC281241
0.8662	High Similarity	NPC86892
0.8662	High Similarity	NPC471909
0.8658	High Similarity	NPC146388
0.8652	High Similarity	NPC133956
0.8652	High Similarity	NPC296624
0.8652	High Similarity	NPC318400
0.8652	High Similarity	NPC185777
0.8652	High Similarity	NPC207002
0.8652	High Similarity	NPC471910
0.8652	High Similarity	NPC167111
0.8643	High Similarity	NPC17343
0.8643	High Similarity	NPC476166
0.8643	High Similarity	NPC268917
0.8643	High Similarity	NPC206224
0.8643	High Similarity	NPC164574
0.8643	High Similarity	NPC12875
0.8643	High Similarity	NPC118114
0.8643	High Similarity	NPC196765
0.8643	High Similarity	NPC150011
0.8643	High Similarity	NPC300875
0.8643	High Similarity	NPC129784
0.8643	High Similarity	NPC236014
0.8643	High Similarity	NPC207892
0.8643	High Similarity	NPC129106
0.8643	High Similarity	NPC280653
0.8643	High Similarity	NPC228369
0.8639	High Similarity	NPC71739
0.8633	High Similarity	NPC168710
0.8633	High Similarity	NPC93962
0.8623	High Similarity	NPC224774
0.8623	High Similarity	NPC121740
0.8623	High Similarity	NPC258567
0.8623	High Similarity	NPC149796
0.8621	High Similarity	NPC170812
0.8621	High Similarity	NPC310370
0.8621	High Similarity	NPC155552
0.8621	High Similarity	NPC183642
0.8621	High Similarity	NPC472523
0.8618	High Similarity	NPC8712
0.8613	High Similarity	NPC471827
0.8613	High Similarity	NPC93219
0.8613	High Similarity	NPC285040
0.8613	High Similarity	NPC168259
0.8613	High Similarity	NPC188022
0.8613	High Similarity	NPC244495
0.8613	High Similarity	NPC102540
0.8613	High Similarity	NPC471828
0.8613	High Similarity	NPC103420
0.8613	High Similarity	NPC17809
0.8611	High Similarity	NPC151946
0.8609	High Similarity	NPC264875
0.8609	High Similarity	NPC309512
0.8609	High Similarity	NPC78835
0.8609	High Similarity	NPC316960
0.8609	High Similarity	NPC163598
0.8609	High Similarity	NPC120774
0.8609	High Similarity	NPC204561
0.8609	High Similarity	NPC317715
0.8609	High Similarity	NPC148945
0.8601	High Similarity	NPC55615
0.8601	High Similarity	NPC149320
0.8601	High Similarity	NPC128529
0.8601	High Similarity	NPC177281
0.8601	High Similarity	NPC188380
0.8601	High Similarity	NPC476455
0.8601	High Similarity	NPC224543
0.8601	High Similarity	NPC471630
0.8601	High Similarity	NPC283019
0.8601	High Similarity	NPC78746
0.8601	High Similarity	NPC160727
0.86	High Similarity	NPC146014
0.86	High Similarity	NPC103116
0.8592	High Similarity	NPC319859
0.8592	High Similarity	NPC84894
0.8592	High Similarity	NPC166672
0.8592	High Similarity	NPC287182
0.8592	High Similarity	NPC267412
0.8592	High Similarity	NPC18804
0.8592	High Similarity	NPC180716
0.8592	High Similarity	NPC260265
0.8592	High Similarity	NPC213173
0.8592	High Similarity	NPC100986
0.8592	High Similarity	NPC62366
0.8592	High Similarity	NPC198381
0.8592	High Similarity	NPC473107
0.8592	High Similarity	NPC127888
0.8592	High Similarity	NPC74655
0.8592	High Similarity	NPC164269
0.8592	High Similarity	NPC47163
0.8592	High Similarity	NPC195343
0.8592	High Similarity	NPC224475
0.8582	High Similarity	NPC13005
0.8581	High Similarity	NPC40222
0.8581	High Similarity	NPC471608
0.8581	High Similarity	NPC268515
0.8571	High Similarity	NPC470225
0.8571	High Similarity	NPC27187
0.8561	High Similarity	NPC274717
0.8561	High Similarity	NPC139595
0.8561	High Similarity	NPC469453
0.8561	High Similarity	NPC293642
0.8561	High Similarity	NPC60704
0.8552	High Similarity	NPC71903
0.8551	High Similarity	NPC471826
0.8551	High Similarity	NPC276212
0.8551	High Similarity	NPC50315
0.8551	High Similarity	NPC230479
0.8551	High Similarity	NPC283049
0.8551	High Similarity	NPC26879
0.8542	High Similarity	NPC155963
0.854	High Similarity	NPC197351
0.854	High Similarity	NPC86502
0.854	High Similarity	NPC27671
0.854	High Similarity	NPC106914
0.854	High Similarity	NPC246648
0.854	High Similarity	NPC201667
0.854	High Similarity	NPC134195

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 NPC43716 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	334
0.1-0.2	972
0.2-0.3	1569
0.3-0.4	2512
0.4-0.5	2070
0.5-0.6	1119
0.6-0.7	381
0.7-0.8	132
0.8-0.85	39
0.85-0.9	17
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8978	High Similarity	NPD4907	Clinical (unspecified phase)
0.8832	High Similarity	NPD4908	Phase 1
0.8786	High Similarity	NPD5123	Clinical (unspecified phase)
0.8786	High Similarity	NPD5124	Phase 1
0.8321	Intermediate Similarity	NPD1610	Phase 2
0.8321	Intermediate Similarity	NPD422	Phase 1
0.8311	Intermediate Similarity	NPD3750	Approved
0.8269	Intermediate Similarity	NPD7768	Phase 2
0.8247	Intermediate Similarity	NPD7411	Suspended
0.8205	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8098	Intermediate Similarity	NPD5844	Phase 1
0.8029	Intermediate Similarity	NPD1548	Phase 1
0.8	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD7075	Discontinued
0.7986	Intermediate Similarity	NPD4625	Phase 3
0.7974	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD3748	Approved
0.7958	Intermediate Similarity	NPD2797	Approved
0.7943	Intermediate Similarity	NPD4749	Approved
0.7931	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD7819	Suspended
0.7908	Intermediate Similarity	NPD7212	Phase 2
0.7908	Intermediate Similarity	NPD7213	Phase 3
0.7885	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1652	Phase 2
0.7857	Intermediate Similarity	NPD7447	Phase 1
0.7857	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6959	Discontinued
0.7834	Intermediate Similarity	NPD4380	Phase 2
0.7823	Intermediate Similarity	NPD4060	Phase 1
0.7815	Intermediate Similarity	NPD1549	Phase 2
0.7808	Intermediate Similarity	NPD3268	Approved
0.7798	Intermediate Similarity	NPD7549	Discontinued
0.7785	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3749	Approved
0.7762	Intermediate Similarity	NPD3225	Approved
0.7748	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD6801	Discontinued
0.7724	Intermediate Similarity	NPD2861	Phase 2
0.7712	Intermediate Similarity	NPD7003	Approved
0.7707	Intermediate Similarity	NPD1653	Approved
0.7703	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD1613	Approved
0.7688	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1551	Phase 2
0.7682	Intermediate Similarity	NPD2796	Approved
0.7654	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1510	Phase 2
0.7597	Intermediate Similarity	NPD4628	Phase 3
0.7591	Intermediate Similarity	NPD5535	Approved
0.7584	Intermediate Similarity	NPD4140	Approved
0.7578	Intermediate Similarity	NPD8455	Phase 2
0.7568	Intermediate Similarity	NPD6798	Discontinued
0.756	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD7097	Phase 1
0.7535	Intermediate Similarity	NPD4626	Approved
0.7532	Intermediate Similarity	NPD5403	Approved
0.7529	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD6599	Discontinued
0.75	Intermediate Similarity	NPD6666	Approved
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD6667	Approved
0.75	Intermediate Similarity	NPD7033	Discontinued
0.75	Intermediate Similarity	NPD4308	Phase 3
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7483	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6232	Discontinued
0.747	Intermediate Similarity	NPD7229	Phase 3
0.7468	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD6273	Approved
0.7466	Intermediate Similarity	NPD3267	Approved
0.7466	Intermediate Similarity	NPD3266	Approved
0.7465	Intermediate Similarity	NPD5691	Approved
0.7452	Intermediate Similarity	NPD6799	Approved
0.7451	Intermediate Similarity	NPD6100	Approved
0.7451	Intermediate Similarity	NPD6099	Approved
0.7451	Intermediate Similarity	NPD2935	Discontinued
0.744	Intermediate Similarity	NPD7473	Discontinued
0.7438	Intermediate Similarity	NPD7458	Discontinued
0.7432	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD4288	Approved
0.7419	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD6355	Discontinued
0.7415	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD37	Approved
0.7407	Intermediate Similarity	NPD1934	Approved
0.7405	Intermediate Similarity	NPD5401	Approved
0.7396	Intermediate Similarity	NPD7228	Approved
0.7394	Intermediate Similarity	NPD6234	Discontinued
0.7383	Intermediate Similarity	NPD3027	Phase 3
0.7378	Intermediate Similarity	NPD4965	Approved
0.7378	Intermediate Similarity	NPD4966	Approved
0.7378	Intermediate Similarity	NPD4967	Phase 2
0.7372	Intermediate Similarity	NPD7466	Approved
0.7368	Intermediate Similarity	NPD1607	Approved
0.7351	Intermediate Similarity	NPD1240	Approved
0.7349	Intermediate Similarity	NPD5494	Approved
0.7341	Intermediate Similarity	NPD8313	Approved
0.7341	Intermediate Similarity	NPD8312	Approved
0.7333	Intermediate Similarity	NPD1296	Phase 2
0.7329	Intermediate Similarity	NPD3226	Approved
0.7317	Intermediate Similarity	NPD5402	Approved
0.7312	Intermediate Similarity	NPD920	Approved
0.7308	Intermediate Similarity	NPD1243	Approved
0.7305	Intermediate Similarity	NPD7199	Phase 2
0.7303	Intermediate Similarity	NPD4340	Discontinued
0.7296	Intermediate Similarity	NPD2533	Approved
0.7296	Intermediate Similarity	NPD2534	Approved
0.7296	Intermediate Similarity	NPD2532	Approved
0.729	Intermediate Similarity	NPD6004	Phase 3
0.729	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5763	Approved
0.729	Intermediate Similarity	NPD6005	Phase 3
0.729	Intermediate Similarity	NPD5762	Approved
0.729	Intermediate Similarity	NPD6002	Phase 3
0.7285	Intermediate Similarity	NPD6233	Phase 2
0.7279	Intermediate Similarity	NPD8651	Approved
0.7278	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1465	Phase 2
0.7251	Intermediate Similarity	NPD7054	Approved
0.7241	Intermediate Similarity	NPD3496	Discontinued
0.7237	Intermediate Similarity	NPD4307	Phase 2
0.723	Intermediate Similarity	NPD1203	Approved
0.7219	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3764	Approved
0.7219	Intermediate Similarity	NPD2313	Discontinued
0.7212	Intermediate Similarity	NPD3817	Phase 2
0.7211	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7472	Approved
0.7209	Intermediate Similarity	NPD7074	Phase 3
0.7205	Intermediate Similarity	NPD7427	Discontinued
0.7202	Intermediate Similarity	NPD8127	Discontinued
0.72	Intermediate Similarity	NPD6832	Phase 2
0.7197	Intermediate Similarity	NPD6674	Discontinued
0.7192	Intermediate Similarity	NPD1611	Approved
0.7188	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7266	Discontinued
0.7179	Intermediate Similarity	NPD2346	Discontinued
0.7168	Intermediate Similarity	NPD6797	Phase 2
0.7168	Intermediate Similarity	NPD5953	Discontinued
0.7153	Intermediate Similarity	NPD3134	Approved
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD2801	Approved
0.7152	Intermediate Similarity	NPD7095	Approved
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7126	Intermediate Similarity	NPD7251	Discontinued
0.7126	Intermediate Similarity	NPD6971	Discontinued
0.7125	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1511	Approved
0.7125	Intermediate Similarity	NPD7041	Phase 2
0.7115	Intermediate Similarity	NPD5404	Approved
0.7115	Intermediate Similarity	NPD5406	Approved
0.7115	Intermediate Similarity	NPD5405	Approved
0.7115	Intermediate Similarity	NPD4477	Approved
0.7115	Intermediate Similarity	NPD5408	Approved
0.7115	Intermediate Similarity	NPD4476	Approved
0.7097	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD4536	Approved
0.7097	Intermediate Similarity	NPD4538	Approved
0.7095	Intermediate Similarity	NPD6583	Phase 3
0.7095	Intermediate Similarity	NPD6582	Phase 2
0.7093	Intermediate Similarity	NPD7177	Discontinued
0.7093	Intermediate Similarity	NPD3818	Discontinued
0.7093	Intermediate Similarity	NPD3751	Discontinued
0.7089	Intermediate Similarity	NPD2800	Approved
0.7088	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7808	Phase 3
0.7086	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD9697	Approved
0.7075	Intermediate Similarity	NPD1091	Approved
0.7073	Intermediate Similarity	NPD6502	Phase 2
0.7067	Intermediate Similarity	NPD6584	Phase 3
0.7066	Intermediate Similarity	NPD3882	Suspended
0.7062	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1778	Approved
0.7052	Intermediate Similarity	NPD7286	Phase 2
0.7047	Intermediate Similarity	NPD1283	Approved
0.7041	Intermediate Similarity	NPD6746	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