NPASS Compound

Structure

NPC268484 OpenBabel07101719252D 37 42 0 0 1 0 0 0 0 0999 V2000 0.8083 -4.2000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0415 -3.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8497 0.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2332 -1.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2332 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4249 -0.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6580 1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0415 -1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6166 -2.8000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.8000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6166 -1.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0415 2.3333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0415 -1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6166 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8083 -3.2667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4249 -1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0415 1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0415 -0.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4249 -1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8083 -1.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6166 -1.8667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.8667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6580 2.3333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8497 2.8000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4249 -0.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2332 -1.8667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8083 -0.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0415 -0.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8083 -1.4000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8083 -0.4667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8497 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4663 2.8000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8497 3.7333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8497 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2332 -2.8000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2332 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 15 1 0 0 0 0 2 35 1 0 0 0 0 3 7 2 0 0 0 0 3 17 1 0 0 0 0 4 8 2 0 0 0 0 4 16 1 0 0 0 0 5 6 2 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 23 1 0 0 0 0 8 28 1 0 0 0 0 9 15 1 0 0 0 0 9 21 1 0 0 0 0 10 15 2 0 0 0 0 11 16 2 0 0 0 0 11 20 1 0 0 0 0 12 17 2 0 0 0 0 12 24 1 0 0 0 0 13 18 2 0 0 0 0 13 26 1 0 0 0 0 14 25 2 0 0 0 0 14 27 1 0 0 0 0 16 25 1 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 26 2 0 0 0 0 20 22 1 0 0 0 0 20 27 2 0 0 0 0 21 19 1 6 0 0 0 21 29 1 0 0 0 0 22 10 1 1 0 0 0 22 29 1 0 0 0 0 23 24 2 0 0 0 0 23 32 1 0 0 0 0 24 33 1 0 0 0 0 25 36 1 0 0 0 0 26 35 1 0 0 0 0 27 37 1 0 0 0 0 28 34 2 0 0 0 0 28 36 1 0 0 0 0 29 30 1 0 0 0 0 30 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.17
Volume:	505.991
LogP:	4.914
LogD:	3.759
LogS:	-4.29
# Rotatable Bonds:	3
TPSA:	109.36
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.184
Synthetic Accessibility Score:	4.217
Fsp3:	0.233
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.066
MDCK Permeability:	1.3947625120636076e-05
Pgp-inhibitor:	0.052
Pgp-substrate:	0.679
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.195
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	96.61311340332031%
Volume Distribution (VD):	0.521
Pgp-substrate:	6.285531044006348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.335
CYP1A2-substrate:	0.908
CYP2C19-inhibitor:	0.941
CYP2C19-substrate:	0.063
CYP2C9-inhibitor:	0.894
CYP2C9-substrate:	0.963
CYP2D6-inhibitor:	0.544
CYP2D6-substrate:	0.875
CYP3A4-inhibitor:	0.696
CYP3A4-substrate:	0.434

ADMET: Excretion

Clearance (CL):	11.216
Half-life (T1/2):	0.425

ADMET: Toxicity

hERG Blockers:	0.123
Human Hepatotoxicity (H-HT):	0.35
Drug-inuced Liver Injury (DILI):	0.928
AMES Toxicity:	0.138
Rat Oral Acute Toxicity:	0.313
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.425
Carcinogencity:	0.113
Eye Corrosion:	0.003
Eye Irritation:	0.387
Respiratory Toxicity:	0.5

Download Data

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

Natural Product: NPC268484

Natural Product ID:	NPC268484
*Common Name:**	Palodesangren B
IUPAC Name:	(4R,4aS,5S,12bR)-5-(3,4-dihydroxyphenyl)-4-(4-hydroxy-2-methoxyphenyl)-2-methyl-4,4a,5,12b-tetrahydro-3H-isochromeno[4,3-g]chromen-9-one
Synonyms:
Standard InCHIKey:	VKFBYVPUKNMLSC-XVIYFPLKSA-N
Standard InCHI:	InChI=1S/C30H26O7/c1-15-9-21(19-6-5-18(31)13-26(19)35-2)29-22(10-15)20-11-16-4-8-28(34)36-25(16)14-27(20)37-30(29)17-3-7-23(32)24(33)12-17/h3-8,10-14,21-22,29-33H,9H2,1-2H3/t21-,22-,29-,30+/m0/s1
SMILES:	CC1=C[C@H]2c3cc4ccc(=O)oc4cc3O[C@H](c3ccc(c(c3)O)O)[C@H]2[C@@H](C1)c1ccc(cc1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL467621
PubChem CID:	10648988
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	4

Activity Type	# Activity
Individual Protein	1
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	=	-8.6	%	PMID[557191]
NPT2	Others	Unspecified		Inhibition	=	0.2	%	PMID[557191]
NPT2	Others	Unspecified		Inhibition	=	8.4	%	PMID[557191]
NPT2	Others	Unspecified		Inhibition	=	19.8	%	PMID[557191]

☑ 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 NPC268484 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	402
0.1-0.2	1663
0.2-0.3	3684
0.3-0.4	8827
0.4-0.5	9741
0.5-0.6	3823
0.6-0.7	5050
0.7-0.8	5136
0.8-0.85	3224
0.85-0.9	1089
0.9-0.95	56
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC223720
0.9384	High Similarity	NPC101255
0.9384	High Similarity	NPC43716
0.9384	High Similarity	NPC475719
0.9211	High Similarity	NPC8712
0.9205	High Similarity	NPC120774
0.9205	High Similarity	NPC163598
0.9205	High Similarity	NPC264875
0.9189	High Similarity	NPC268515
0.9189	High Similarity	NPC40222
0.9128	High Similarity	NPC476347
0.9067	High Similarity	NPC476348
0.9067	High Similarity	NPC187398
0.9032	High Similarity	NPC125495
0.9007	High Similarity	NPC176903
0.9007	High Similarity	NPC30688
0.8947	High Similarity	NPC294522
0.8947	High Similarity	NPC120426
0.8947	High Similarity	NPC205727
0.8947	High Similarity	NPC21184
0.8924	High Similarity	NPC12326
0.8904	High Similarity	NPC474886
0.8861	High Similarity	NPC139540
0.8861	High Similarity	NPC177100
0.8861	High Similarity	NPC109061
0.8854	High Similarity	NPC7543
0.8854	High Similarity	NPC94220
0.8854	High Similarity	NPC166456
0.8854	High Similarity	NPC24339
0.8854	High Similarity	NPC98083
0.8846	High Similarity	NPC165483
0.8831	High Similarity	NPC176186
0.8831	High Similarity	NPC169404
0.8831	High Similarity	NPC53587
0.88	High Similarity	NPC471763
0.8792	High Similarity	NPC204347
0.8792	High Similarity	NPC59841
0.8792	High Similarity	NPC475891
0.8792	High Similarity	NPC2613
0.8774	High Similarity	NPC150442
0.8774	High Similarity	NPC115203
0.8774	High Similarity	NPC474656
0.8774	High Similarity	NPC470769
0.8767	High Similarity	NPC473413
0.8758	High Similarity	NPC211561
0.875	High Similarity	NPC204770
0.875	High Similarity	NPC294558
0.875	High Similarity	NPC108811
0.875	High Similarity	NPC170103
0.875	High Similarity	NPC58190
0.875	High Similarity	NPC262911
0.875	High Similarity	NPC18185
0.875	High Similarity	NPC15577
0.875	High Similarity	NPC70409
0.875	High Similarity	NPC236202
0.875	High Similarity	NPC82917
0.875	High Similarity	NPC202742
0.875	High Similarity	NPC263940
0.8742	High Similarity	NPC155754
0.8742	High Similarity	NPC163898
0.8742	High Similarity	NPC124747
0.8742	High Similarity	NPC469701
0.8733	High Similarity	NPC7439
0.8733	High Similarity	NPC256555
0.8733	High Similarity	NPC110067
0.8733	High Similarity	NPC34245
0.8733	High Similarity	NPC91492
0.8725	High Similarity	NPC178054
0.8725	High Similarity	NPC265075
0.8716	High Similarity	NPC260741
0.8716	High Similarity	NPC70682
0.8716	High Similarity	NPC32630
0.8701	High Similarity	NPC477612
0.8693	High Similarity	NPC473408
0.8693	High Similarity	NPC102934
0.8693	High Similarity	NPC20757
0.8693	High Similarity	NPC227516
0.8693	High Similarity	NPC252402
0.8684	High Similarity	NPC233980
0.8684	High Similarity	NPC96576
0.8675	High Similarity	NPC473108
0.8675	High Similarity	NPC471824
0.8671	High Similarity	NPC470827
0.8667	High Similarity	NPC20631
0.8667	High Similarity	NPC93640
0.8654	High Similarity	NPC475141
0.8649	High Similarity	NPC38874
0.8636	High Similarity	NPC475250
0.863	High Similarity	NPC11060
0.8627	High Similarity	NPC97937
0.8627	High Similarity	NPC21776
0.8627	High Similarity	NPC170239
0.8627	High Similarity	NPC16269
0.8627	High Similarity	NPC275125
0.8618	High Similarity	NPC469557
0.8616	High Similarity	NPC470828
0.8616	High Similarity	NPC478269
0.8608	High Similarity	NPC318432
0.86	High Similarity	NPC195357
0.86	High Similarity	NPC152771
0.86	High Similarity	NPC138149
0.86	High Similarity	NPC287286
0.86	High Similarity	NPC35216
0.8599	High Similarity	NPC7178
0.8599	High Similarity	NPC62903
0.8599	High Similarity	NPC473736
0.8591	High Similarity	NPC35501
0.8591	High Similarity	NPC47040
0.8591	High Similarity	NPC144512
0.8591	High Similarity	NPC37428
0.8591	High Similarity	NPC137262
0.8591	High Similarity	NPC279573
0.8591	High Similarity	NPC278600
0.859	High Similarity	NPC215060
0.859	High Similarity	NPC134911
0.859	High Similarity	NPC44192
0.859	High Similarity	NPC469944
0.859	High Similarity	NPC322899
0.859	High Similarity	NPC46283
0.859	High Similarity	NPC272552
0.859	High Similarity	NPC226108
0.859	High Similarity	NPC476352
0.8581	High Similarity	NPC265433
0.8581	High Similarity	NPC26954
0.8581	High Similarity	NPC38099
0.8581	High Similarity	NPC234952
0.8581	High Similarity	NPC470802
0.8581	High Similarity	NPC162659
0.8581	High Similarity	NPC270456
0.8581	High Similarity	NPC248727
0.858	High Similarity	NPC142614
0.8571	High Similarity	NPC236166
0.8571	High Similarity	NPC50896
0.8571	High Similarity	NPC204353
0.8571	High Similarity	NPC131950
0.8571	High Similarity	NPC326600
0.8562	High Similarity	NPC260397
0.8562	High Similarity	NPC24164
0.8562	High Similarity	NPC53889
0.8553	High Similarity	NPC45257
0.8553	High Similarity	NPC289322
0.8553	High Similarity	NPC38779
0.8553	High Similarity	NPC93323
0.8553	High Similarity	NPC114179
0.8553	High Similarity	NPC68324
0.8553	High Similarity	NPC473845
0.8553	High Similarity	NPC280092
0.8553	High Similarity	NPC12641
0.8553	High Similarity	NPC156818
0.8553	High Similarity	NPC36732
0.8553	High Similarity	NPC160512
0.8544	High Similarity	NPC142479
0.8544	High Similarity	NPC155015
0.8543	High Similarity	NPC131971
0.8543	High Similarity	NPC67467
0.8535	High Similarity	NPC20050
0.8535	High Similarity	NPC306267
0.8535	High Similarity	NPC149735
0.8533	High Similarity	NPC22317
0.8533	High Similarity	NPC259519
0.8533	High Similarity	NPC312881
0.8533	High Similarity	NPC309124
0.8533	High Similarity	NPC184797
0.8528	High Similarity	NPC471823
0.8528	High Similarity	NPC9309
0.8526	High Similarity	NPC2745
0.8523	High Similarity	NPC232246
0.8523	High Similarity	NPC225106
0.8523	High Similarity	NPC281014
0.8523	High Similarity	NPC153818
0.8523	High Similarity	NPC184861
0.8523	High Similarity	NPC126206
0.8523	High Similarity	NPC211549
0.8523	High Similarity	NPC294456
0.8523	High Similarity	NPC212124
0.8516	High Similarity	NPC113790
0.8514	High Similarity	NPC151224
0.8514	High Similarity	NPC470356
0.8514	High Similarity	NPC474206
0.8514	High Similarity	NPC94750
0.8514	High Similarity	NPC121812
0.8514	High Similarity	NPC112246
0.8514	High Similarity	NPC112939
0.8509	High Similarity	NPC478267
0.8506	High Similarity	NPC474397
0.8506	High Similarity	NPC178129
0.8506	High Similarity	NPC231149
0.8503	High Similarity	NPC31849
0.85	High Similarity	NPC87317
0.8497	Intermediate Similarity	NPC472457
0.8497	Intermediate Similarity	NPC108994
0.8497	Intermediate Similarity	NPC106126
0.8497	Intermediate Similarity	NPC90645
0.8497	Intermediate Similarity	NPC125617
0.8494	Intermediate Similarity	NPC98583
0.8491	Intermediate Similarity	NPC250436
0.8491	Intermediate Similarity	NPC104983
0.8491	Intermediate Similarity	NPC300845
0.8491	Intermediate Similarity	NPC88803
0.8491	Intermediate Similarity	NPC291948

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 NPC268484 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	361
0.1-0.2	956
0.2-0.3	1779
0.3-0.4	2593
0.4-0.5	1881
0.5-0.6	1012
0.6-0.7	382
0.7-0.8	128
0.8-0.85	44
0.85-0.9	14
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8491	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8425	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8424	Intermediate Similarity	NPD5844	Phase 1
0.8311	Intermediate Similarity	NPD1613	Approved
0.8311	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8288	Intermediate Similarity	NPD4908	Phase 1
0.828	Intermediate Similarity	NPD1653	Approved
0.8255	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD5124	Phase 1
0.825	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD7549	Discontinued
0.8095	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6166	Phase 2
0.8024	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3027	Phase 3
0.7963	Intermediate Similarity	NPD1934	Approved
0.7949	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD6234	Discontinued
0.7929	Intermediate Similarity	NPD7228	Approved
0.7834	Intermediate Similarity	NPD3750	Approved
0.7829	Intermediate Similarity	NPD4060	Phase 1
0.7818	Intermediate Similarity	NPD7768	Phase 2
0.7808	Intermediate Similarity	NPD422	Phase 1
0.7808	Intermediate Similarity	NPD1610	Phase 2
0.7805	Intermediate Similarity	NPD1465	Phase 2
0.7798	Intermediate Similarity	NPD6232	Discontinued
0.7791	Intermediate Similarity	NPD7411	Suspended
0.7778	Intermediate Similarity	NPD7054	Approved
0.7771	Intermediate Similarity	NPD7075	Discontinued
0.7771	Intermediate Similarity	NPD1652	Phase 2
0.7765	Intermediate Similarity	NPD7473	Discontinued
0.7758	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD7266	Discontinued
0.7748	Intermediate Similarity	NPD4625	Phase 3
0.7744	Intermediate Similarity	NPD37	Approved
0.7738	Intermediate Similarity	NPD6959	Discontinued
0.7733	Intermediate Similarity	NPD7472	Approved
0.7733	Intermediate Similarity	NPD7074	Phase 3
0.773	Intermediate Similarity	NPD4380	Phase 2
0.7711	Intermediate Similarity	NPD4966	Approved
0.7711	Intermediate Similarity	NPD4967	Phase 2
0.7711	Intermediate Similarity	NPD4965	Approved
0.7706	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4749	Approved
0.7697	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7819	Suspended
0.7697	Intermediate Similarity	NPD2801	Approved
0.7688	Intermediate Similarity	NPD6797	Phase 2
0.7688	Intermediate Similarity	NPD1511	Approved
0.7679	Intermediate Similarity	NPD5494	Approved
0.7669	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6674	Discontinued
0.7651	Intermediate Similarity	NPD3817	Phase 2
0.7644	Intermediate Similarity	NPD7251	Discontinued
0.7644	Intermediate Similarity	NPD6559	Discontinued
0.764	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7199	Phase 2
0.7616	Intermediate Similarity	NPD3818	Discontinued
0.7616	Intermediate Similarity	NPD2861	Phase 2
0.761	Intermediate Similarity	NPD8166	Discontinued
0.76	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1512	Approved
0.7571	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.756	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1548	Phase 1
0.7531	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD6801	Discontinued
0.7529	Intermediate Similarity	NPD8127	Discontinued
0.7516	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD7808	Phase 3
0.7485	Intermediate Similarity	NPD8455	Phase 2
0.7483	Intermediate Similarity	NPD2797	Approved
0.7471	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7213	Phase 3
0.7469	Intermediate Similarity	NPD7212	Phase 2
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD8312	Approved
0.7458	Intermediate Similarity	NPD8313	Approved
0.7443	Intermediate Similarity	NPD7240	Approved
0.744	Intermediate Similarity	NPD5402	Approved
0.7423	Intermediate Similarity	NPD7447	Phase 1
0.7391	Intermediate Similarity	NPD4628	Phase 3
0.7384	Intermediate Similarity	NPD7229	Phase 3
0.7375	Intermediate Similarity	NPD1549	Phase 2
0.7372	Intermediate Similarity	NPD4140	Approved
0.7358	Intermediate Similarity	NPD2935	Discontinued
0.7355	Intermediate Similarity	NPD6798	Discontinued
0.7355	Intermediate Similarity	NPD3268	Approved
0.7353	Intermediate Similarity	NPD3749	Approved
0.7349	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6190	Approved
0.7342	Intermediate Similarity	NPD7097	Phase 1
0.7333	Intermediate Similarity	NPD5403	Approved
0.7325	Intermediate Similarity	NPD230	Phase 1
0.7315	Intermediate Similarity	NPD4626	Approved
0.7314	Intermediate Similarity	NPD3751	Discontinued
0.7312	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5762	Approved
0.7312	Intermediate Similarity	NPD5763	Approved
0.7312	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD6599	Discontinued
0.7303	Intermediate Similarity	NPD3225	Approved
0.7284	Intermediate Similarity	NPD7003	Approved
0.7273	Intermediate Similarity	NPD6273	Approved
0.7267	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6799	Approved
0.725	Intermediate Similarity	NPD2796	Approved
0.725	Intermediate Similarity	NPD6100	Approved
0.725	Intermediate Similarity	NPD6099	Approved
0.725	Intermediate Similarity	NPD1551	Phase 2
0.7248	Intermediate Similarity	NPD5691	Approved
0.7246	Intermediate Similarity	NPD3226	Approved
0.7237	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6355	Discontinued
0.7212	Intermediate Similarity	NPD2533	Approved
0.7212	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5401	Approved
0.7212	Intermediate Similarity	NPD2532	Approved
0.7212	Intermediate Similarity	NPD2534	Approved
0.7209	Intermediate Similarity	NPD919	Approved
0.7208	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6233	Phase 2
0.7188	Intermediate Similarity	NPD1510	Phase 2
0.7179	Intermediate Similarity	NPD7095	Approved
0.7174	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7680	Approved
0.7152	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3620	Phase 2
0.7152	Intermediate Similarity	NPD3496	Discontinued
0.7151	Intermediate Similarity	NPD7685	Pre-registration
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7128	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5535	Approved
0.7108	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD4340	Discontinued
0.7105	Intermediate Similarity	NPD1611	Approved
0.7099	Intermediate Similarity	NPD2346	Discontinued
0.7091	Intermediate Similarity	NPD6667	Approved
0.7091	Intermediate Similarity	NPD6666	Approved
0.7086	Intermediate Similarity	NPD3787	Discontinued
0.7081	Intermediate Similarity	NPD4308	Phase 3
0.7081	Intermediate Similarity	NPD7033	Discontinued
0.7081	Intermediate Similarity	NPD2799	Discontinued
0.7078	Intermediate Similarity	NPD8651	Approved
0.7073	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD4110	Phase 3
0.7055	Intermediate Similarity	NPD2424	Discontinued
0.7051	Intermediate Similarity	NPD3018	Phase 2
0.7049	Intermediate Similarity	NPD8150	Discontinued
0.7035	Intermediate Similarity	NPD4288	Approved
0.7033	Intermediate Similarity	NPD8053	Approved
0.7033	Intermediate Similarity	NPD8054	Approved
0.7033	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD3266	Approved
0.7032	Intermediate Similarity	NPD3267	Approved
0.7024	Intermediate Similarity	NPD920	Approved
0.7019	Intermediate Similarity	NPD4538	Approved
0.7019	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4536	Approved
0.7013	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4481	Phase 3
0.7006	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5735	Approved
0.7	Intermediate Similarity	NPD447	Suspended
0.6994	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6004	Phase 3
0.6994	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD6002	Phase 3
0.6994	Remote Similarity	NPD6005	Phase 3
0.6993	Remote Similarity	NPD1091	Approved
0.6978	Remote Similarity	NPD7312	Approved
0.6978	Remote Similarity	NPD7311	Approved
0.6978	Remote Similarity	NPD7313	Approved
0.6978	Remote Similarity	NPD7310	Approved
0.6974	Remote Similarity	NPD8151	Discontinued
0.6971	Remote Similarity	NPD6746	Phase 2
0.6971	Remote Similarity	NPD4666	Phase 3
0.697	Remote Similarity	NPD7466	Approved
0.6961	Remote Similarity	NPD7038	Approved
0.6961	Remote Similarity	NPD7039	Approved
0.6959	Remote Similarity	NPD5283	Phase 1
0.6957	Remote Similarity	NPD1607	Approved
0.6954	Remote Similarity	NPD6971	Discontinued

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