NPASS Compound

Structure

NPC223720 OpenBabel07101718182D 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 -0.8083 -2.3333 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 -5.6580 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 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 -4.8497 0.0000 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 -3.2332 -0.9333 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 -1.6166 1.8667 0.0000 C 0 0 1 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 0.0000 1.8667 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4663 -0.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4663 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 -1.6166 -0.9333 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 -4.0415 -1.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2746 -1.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2746 0.4667 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 -0.8083 -1.4000 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 16 1 0 0 0 0 4 8 2 0 0 0 0 4 17 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 20 1 0 0 0 0 10 15 2 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 16 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 17 25 1 0 0 0 0 18 31 1 0 0 0 0 19 26 2 0 0 0 0 19 30 1 0 0 0 0 20 16 1 6 0 0 0 20 29 1 0 0 0 0 21 22 1 0 0 0 0 21 27 2 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:	600.4
Volume:	639.415
LogP:	4.623
LogD:	4.042
LogS:	-5.029
# Rotatable Bonds:	8
TPSA:	113.29
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.246
Synthetic Accessibility Score:	5.34
Fsp3:	0.833
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:	-5.142
MDCK Permeability:	1.0951257536362391e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.055
30% Bioavailability (F30%):	0.448

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	89.76654052734375%
Volume Distribution (VD):	1.286
Pgp-substrate:	2.485410451889038%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.504
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.132
CYP2C9-substrate:	0.697
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.689
CYP3A4-inhibitor:	0.349
CYP3A4-substrate:	0.446

ADMET: Excretion

Clearance (CL):	3.63
Half-life (T1/2):	0.168

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.216
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.05
Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.588
Skin Sensitization:	0.046
Carcinogencity:	0.045
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.923

Download Data

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

Natural Product: NPC223720

Natural Product ID:	NPC223720
*Common Name:**	Palodesangren A
IUPAC Name:	(4R,4aS,5S,12bR)-4-(3,4-dihydroxyphenyl)-5-(4-hydroxy-2-methoxyphenyl)-2-methyl-4,4a,5,12b-tetrahydro-3H-isochromeno[4,3-g]chromen-9-one
Synonyms:
Standard InCHIKey:	AAEFZQHINRCTBX-ZHOVMQETSA-N
Standard InCHI:	InChI=1S/C30H26O7/c1-15-9-20(16-3-7-23(32)24(33)12-16)29-22(10-15)21-11-17-4-8-28(34)36-25(17)14-27(21)37-30(29)19-6-5-18(31)13-26(19)35-2/h3-8,10-14,20,22,29-33H,9H2,1-2H3/t20-,22-,29-,30+/m0/s1
SMILES:	COc1cc(O)ccc1[C@H]1Oc2cc3oc(=O)ccc3cc2[C@H]2[C@@H]1[C@@H](CC(=C2)C)c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511740
PubChem CID:	10696654
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	=	-30.4	%	PMID[526696]
NPT2	Others	Unspecified		Inhibition	=	0.3	%	PMID[526696]
NPT2	Others	Unspecified		Inhibition	=	4.8	%	PMID[526696]
NPT2	Others	Unspecified		Inhibition	=	5.2	%	PMID[526696]

☑ 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 NPC223720 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	398
0.1-0.2	1681
0.2-0.3	3751
0.3-0.4	8955
0.4-0.5	9568
0.5-0.6	3819
0.6-0.7	5183
0.7-0.8	5133
0.8-0.85	3228
0.85-0.9	942
0.9-0.95	37
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC268484
0.9448	High Similarity	NPC475719
0.9448	High Similarity	NPC43716
0.9448	High Similarity	NPC101255
0.9145	High Similarity	NPC8712
0.9139	High Similarity	NPC120774
0.9139	High Similarity	NPC163598
0.9139	High Similarity	NPC264875
0.9122	High Similarity	NPC268515
0.9122	High Similarity	NPC40222
0.906	High Similarity	NPC476347
0.9	High Similarity	NPC476348
0.9	High Similarity	NPC187398
0.8968	High Similarity	NPC125495
0.8966	High Similarity	NPC474886
0.894	High Similarity	NPC30688
0.894	High Similarity	NPC176903
0.8882	High Similarity	NPC294522
0.8882	High Similarity	NPC120426
0.8882	High Similarity	NPC21184
0.8882	High Similarity	NPC205727
0.8861	High Similarity	NPC12326
0.8797	High Similarity	NPC139540
0.8797	High Similarity	NPC177100
0.8797	High Similarity	NPC109061
0.879	High Similarity	NPC24339
0.879	High Similarity	NPC166456
0.879	High Similarity	NPC94220
0.879	High Similarity	NPC7543
0.879	High Similarity	NPC98083
0.8782	High Similarity	NPC165483
0.8766	High Similarity	NPC176186
0.8766	High Similarity	NPC169404
0.8766	High Similarity	NPC53587
0.8733	High Similarity	NPC471763
0.8725	High Similarity	NPC204347
0.8725	High Similarity	NPC93640
0.8725	High Similarity	NPC59841
0.8725	High Similarity	NPC20631
0.8725	High Similarity	NPC2613
0.8725	High Similarity	NPC475891
0.871	High Similarity	NPC470769
0.871	High Similarity	NPC150442
0.871	High Similarity	NPC474656
0.871	High Similarity	NPC115203
0.8699	High Similarity	NPC473413
0.8693	High Similarity	NPC211561
0.8684	High Similarity	NPC262911
0.8684	High Similarity	NPC294558
0.8684	High Similarity	NPC236202
0.8684	High Similarity	NPC15577
0.8684	High Similarity	NPC18185
0.8684	High Similarity	NPC58190
0.8684	High Similarity	NPC204770
0.8684	High Similarity	NPC82917
0.8684	High Similarity	NPC263940
0.8684	High Similarity	NPC170103
0.8684	High Similarity	NPC70409
0.8684	High Similarity	NPC202742
0.8684	High Similarity	NPC108811
0.8679	High Similarity	NPC124747
0.8679	High Similarity	NPC155754
0.8675	High Similarity	NPC163898
0.8675	High Similarity	NPC469701
0.8667	High Similarity	NPC110067
0.8667	High Similarity	NPC91492
0.8667	High Similarity	NPC7439
0.8667	High Similarity	NPC34245
0.8667	High Similarity	NPC256555
0.8658	High Similarity	NPC138149
0.8658	High Similarity	NPC265075
0.8658	High Similarity	NPC178054
0.8649	High Similarity	NPC37428
0.8649	High Similarity	NPC47040
0.8649	High Similarity	NPC70682
0.8649	High Similarity	NPC260741
0.8649	High Similarity	NPC278600
0.8649	High Similarity	NPC35501
0.8649	High Similarity	NPC144512
0.8649	High Similarity	NPC137262
0.8649	High Similarity	NPC32630
0.8636	High Similarity	NPC477612
0.863	High Similarity	NPC131950
0.8627	High Similarity	NPC20757
0.8627	High Similarity	NPC227516
0.8627	High Similarity	NPC473408
0.8627	High Similarity	NPC252402
0.8627	High Similarity	NPC102934
0.8618	High Similarity	NPC96576
0.8618	High Similarity	NPC233980
0.8609	High Similarity	NPC471824
0.8609	High Similarity	NPC473108
0.8608	High Similarity	NPC470827
0.859	High Similarity	NPC475141
0.8581	High Similarity	NPC38874
0.8571	High Similarity	NPC475250
0.8562	High Similarity	NPC16269
0.8562	High Similarity	NPC21776
0.8562	High Similarity	NPC275125
0.8562	High Similarity	NPC170239
0.8562	High Similarity	NPC97937
0.8562	High Similarity	NPC11060
0.8553	High Similarity	NPC469557
0.8553	High Similarity	NPC478269
0.8553	High Similarity	NPC470828
0.8544	High Similarity	NPC318432
0.8535	High Similarity	NPC473736
0.8535	High Similarity	NPC7178
0.8535	High Similarity	NPC62903
0.8533	High Similarity	NPC287286
0.8533	High Similarity	NPC195357
0.8533	High Similarity	NPC152771
0.8533	High Similarity	NPC35216
0.8526	High Similarity	NPC44192
0.8526	High Similarity	NPC469944
0.8526	High Similarity	NPC226108
0.8526	High Similarity	NPC272552
0.8526	High Similarity	NPC46283
0.8526	High Similarity	NPC322899
0.8526	High Similarity	NPC134911
0.8526	High Similarity	NPC476352
0.8526	High Similarity	NPC215060
0.8523	High Similarity	NPC279573
0.8519	High Similarity	NPC142614
0.8514	High Similarity	NPC162659
0.8514	High Similarity	NPC234952
0.8514	High Similarity	NPC270456
0.8514	High Similarity	NPC470802
0.8514	High Similarity	NPC248727
0.8514	High Similarity	NPC265433
0.8514	High Similarity	NPC26954
0.8514	High Similarity	NPC38099
0.8506	High Similarity	NPC236166
0.8506	High Similarity	NPC142863
0.8503	High Similarity	NPC50896
0.8503	High Similarity	NPC326600
0.8503	High Similarity	NPC204353
0.8503	High Similarity	NPC317380
0.8503	High Similarity	NPC92830
0.8503	High Similarity	NPC111635
0.85	High Similarity	NPC53889
0.85	High Similarity	NPC24164
0.8497	Intermediate Similarity	NPC260397
0.8491	Intermediate Similarity	NPC289322
0.8491	Intermediate Similarity	NPC68324
0.8491	Intermediate Similarity	NPC114179
0.8491	Intermediate Similarity	NPC38779
0.8491	Intermediate Similarity	NPC156818
0.8491	Intermediate Similarity	NPC160512
0.8487	Intermediate Similarity	NPC36732
0.8487	Intermediate Similarity	NPC473845
0.8487	Intermediate Similarity	NPC280092
0.8487	Intermediate Similarity	NPC12641
0.8487	Intermediate Similarity	NPC45257
0.8487	Intermediate Similarity	NPC93323
0.8483	Intermediate Similarity	NPC32463
0.8481	Intermediate Similarity	NPC155015
0.8481	Intermediate Similarity	NPC142479
0.8477	Intermediate Similarity	NPC67467
0.8477	Intermediate Similarity	NPC131971
0.8471	Intermediate Similarity	NPC149735
0.8471	Intermediate Similarity	NPC20050
0.8471	Intermediate Similarity	NPC306267
0.8467	Intermediate Similarity	NPC309124
0.8467	Intermediate Similarity	NPC312881
0.8467	Intermediate Similarity	NPC184797
0.8467	Intermediate Similarity	NPC259519
0.8467	Intermediate Similarity	NPC22317
0.8466	Intermediate Similarity	NPC471823
0.8466	Intermediate Similarity	NPC9309
0.8462	Intermediate Similarity	NPC2745
0.8456	Intermediate Similarity	NPC153818
0.8456	Intermediate Similarity	NPC184861
0.8456	Intermediate Similarity	NPC232246
0.8456	Intermediate Similarity	NPC131198
0.8456	Intermediate Similarity	NPC294456
0.8456	Intermediate Similarity	NPC211549
0.8456	Intermediate Similarity	NPC212124
0.8456	Intermediate Similarity	NPC306365
0.8456	Intermediate Similarity	NPC225106
0.8456	Intermediate Similarity	NPC126206
0.8456	Intermediate Similarity	NPC281014
0.8452	Intermediate Similarity	NPC113790
0.8447	Intermediate Similarity	NPC478267
0.8446	Intermediate Similarity	NPC121812
0.8446	Intermediate Similarity	NPC94750
0.8446	Intermediate Similarity	NPC112939
0.8446	Intermediate Similarity	NPC151224
0.8446	Intermediate Similarity	NPC112246
0.8446	Intermediate Similarity	NPC470356
0.8446	Intermediate Similarity	NPC474206
0.8442	Intermediate Similarity	NPC474397
0.8442	Intermediate Similarity	NPC178129
0.8442	Intermediate Similarity	NPC231149
0.8438	Intermediate Similarity	NPC87317
0.8435	Intermediate Similarity	NPC31849
0.8435	Intermediate Similarity	NPC469955
0.8435	Intermediate Similarity	NPC469952
0.8435	Intermediate Similarity	NPC185777
0.8434	Intermediate Similarity	NPC98583

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 NPC223720 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	353
0.1-0.2	974
0.2-0.3	1751
0.3-0.4	2588
0.4-0.5	1890
0.5-0.6	1035
0.6-0.7	371
0.7-0.8	128
0.8-0.85	46
0.85-0.9	14
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8483	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8428	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD5844	Phase 1
0.8345	Intermediate Similarity	NPD4908	Phase 1
0.8311	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.8311	Intermediate Similarity	NPD5124	Phase 1
0.8243	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD1613	Approved
0.8217	Intermediate Similarity	NPD1653	Approved
0.8187	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7549	Discontinued
0.8027	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6166	Phase 2
0.7964	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD3027	Phase 3
0.7901	Intermediate Similarity	NPD1934	Approved
0.7885	Intermediate Similarity	NPD3750	Approved
0.7881	Intermediate Similarity	NPD4060	Phase 1
0.7879	Intermediate Similarity	NPD6234	Discontinued
0.787	Intermediate Similarity	NPD7228	Approved
0.7866	Intermediate Similarity	NPD7768	Phase 2
0.7862	Intermediate Similarity	NPD1610	Phase 2
0.7862	Intermediate Similarity	NPD422	Phase 1
0.784	Intermediate Similarity	NPD7411	Suspended
0.7818	Intermediate Similarity	NPD7075	Discontinued
0.7805	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD4625	Phase 3
0.7755	Intermediate Similarity	NPD4749	Approved
0.7751	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD1465	Phase 2
0.7744	Intermediate Similarity	NPD7819	Suspended
0.7744	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6232	Discontinued
0.7719	Intermediate Similarity	NPD7054	Approved
0.7716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1652	Phase 2
0.7706	Intermediate Similarity	NPD7473	Discontinued
0.7692	Intermediate Similarity	NPD7266	Discontinued
0.7688	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD37	Approved
0.7679	Intermediate Similarity	NPD7199	Phase 2
0.7679	Intermediate Similarity	NPD6959	Discontinued
0.7674	Intermediate Similarity	NPD7472	Approved
0.7674	Intermediate Similarity	NPD7074	Phase 3
0.7669	Intermediate Similarity	NPD4380	Phase 2
0.7658	Intermediate Similarity	NPD8166	Discontinued
0.7651	Intermediate Similarity	NPD4965	Approved
0.7651	Intermediate Similarity	NPD4966	Approved
0.7651	Intermediate Similarity	NPD4967	Phase 2
0.7636	Intermediate Similarity	NPD2801	Approved
0.763	Intermediate Similarity	NPD6797	Phase 2
0.7625	Intermediate Similarity	NPD1511	Approved
0.7619	Intermediate Similarity	NPD5494	Approved
0.7595	Intermediate Similarity	NPD6674	Discontinued
0.7595	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD3817	Phase 2
0.7588	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7251	Discontinued
0.7586	Intermediate Similarity	NPD6559	Discontinued
0.7586	Intermediate Similarity	NPD1548	Phase 1
0.7584	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6801	Discontinued
0.7564	Intermediate Similarity	NPD3748	Approved
0.7558	Intermediate Similarity	NPD3818	Discontinued
0.755	Intermediate Similarity	NPD2861	Phase 2
0.7545	Intermediate Similarity	NPD3882	Suspended
0.7543	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD2797	Approved
0.7531	Intermediate Similarity	NPD1512	Approved
0.7516	Intermediate Similarity	NPD7212	Phase 2
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD7213	Phase 3
0.7514	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD8127	Discontinued
0.7469	Intermediate Similarity	NPD7447	Phase 1
0.7469	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD7808	Phase 3
0.7438	Intermediate Similarity	NPD4628	Phase 3
0.7425	Intermediate Similarity	NPD8455	Phase 2
0.7421	Intermediate Similarity	NPD1549	Phase 2
0.7419	Intermediate Similarity	NPD4140	Approved
0.7414	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD6798	Discontinued
0.7403	Intermediate Similarity	NPD3268	Approved
0.7401	Intermediate Similarity	NPD8313	Approved
0.7401	Intermediate Similarity	NPD8312	Approved
0.7396	Intermediate Similarity	NPD3749	Approved
0.7394	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7240	Approved
0.7381	Intermediate Similarity	NPD5402	Approved
0.7378	Intermediate Similarity	NPD5403	Approved
0.7365	Intermediate Similarity	NPD4626	Approved
0.7358	Intermediate Similarity	NPD5763	Approved
0.7358	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD5762	Approved
0.7351	Intermediate Similarity	NPD3225	Approved
0.7349	Intermediate Similarity	NPD6599	Discontinued
0.7329	Intermediate Similarity	NPD7003	Approved
0.7326	Intermediate Similarity	NPD7229	Phase 3
0.7317	Intermediate Similarity	NPD6273	Approved
0.7312	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6799	Approved
0.7301	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5691	Approved
0.7296	Intermediate Similarity	NPD6100	Approved
0.7296	Intermediate Similarity	NPD2796	Approved
0.7296	Intermediate Similarity	NPD6099	Approved
0.7296	Intermediate Similarity	NPD1551	Phase 2
0.7296	Intermediate Similarity	NPD2935	Discontinued
0.7285	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6190	Approved
0.7278	Intermediate Similarity	NPD7097	Phase 1
0.7273	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6355	Discontinued
0.7261	Intermediate Similarity	NPD230	Phase 1
0.7257	Intermediate Similarity	NPD3751	Discontinued
0.7256	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD5401	Approved
0.7255	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD919	Approved
0.7233	Intermediate Similarity	NPD1510	Phase 2
0.7226	Intermediate Similarity	NPD7095	Approved
0.7197	Intermediate Similarity	NPD3620	Phase 2
0.7197	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7458	Discontinued
0.7186	Intermediate Similarity	NPD3226	Approved
0.7172	Intermediate Similarity	NPD5535	Approved
0.7152	Intermediate Similarity	NPD4340	Discontinued
0.7152	Intermediate Similarity	NPD2534	Approved
0.7152	Intermediate Similarity	NPD2532	Approved
0.7152	Intermediate Similarity	NPD2533	Approved
0.7134	Intermediate Similarity	NPD6666	Approved
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7134	Intermediate Similarity	NPD6667	Approved
0.7125	Intermediate Similarity	NPD2799	Discontinued
0.7125	Intermediate Similarity	NPD7033	Discontinued
0.7125	Intermediate Similarity	NPD4308	Phase 3
0.7124	Intermediate Similarity	NPD8651	Approved
0.712	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD4110	Phase 3
0.7117	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7680	Approved
0.7097	Intermediate Similarity	NPD3018	Phase 2
0.7095	Intermediate Similarity	NPD7685	Pre-registration
0.7086	Intermediate Similarity	NPD3496	Discontinued
0.7078	Intermediate Similarity	NPD3266	Approved
0.7078	Intermediate Similarity	NPD3267	Approved
0.7076	Intermediate Similarity	NPD4288	Approved
0.7074	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8054	Approved
0.7072	Intermediate Similarity	NPD8053	Approved
0.7072	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4481	Phase 3
0.7044	Intermediate Similarity	NPD5735	Approved
0.7039	Intermediate Similarity	NPD1611	Approved
0.7037	Intermediate Similarity	NPD2346	Discontinued
0.7029	Intermediate Similarity	NPD3787	Discontinued
0.7012	Intermediate Similarity	NPD7466	Approved
0.7011	Intermediate Similarity	NPD4666	Phase 3
0.7007	Intermediate Similarity	NPD5283	Phase 1
0.7	Intermediate Similarity	NPD1607	Approved
0.6995	Remote Similarity	NPD8150	Discontinued
0.6994	Remote Similarity	NPD2424	Discontinued
0.6994	Remote Similarity	NPD6971	Discontinued
0.6993	Remote Similarity	NPD1608	Approved
0.6988	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7041	Phase 2
0.6981	Remote Similarity	NPD1240	Approved
0.6975	Remote Similarity	NPD5408	Approved
0.6975	Remote Similarity	NPD5404	Approved
0.6975	Remote Similarity	NPD5406	Approved
0.6975	Remote Similarity	NPD5405	Approved
0.6968	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3022	Approved
0.6966	Remote Similarity	NPD7177	Discontinued
0.6966	Remote Similarity	NPD3021	Approved
0.6964	Remote Similarity	NPD920	Approved
0.6962	Remote Similarity	NPD1296	Phase 2
0.6957	Remote Similarity	NPD4536	Approved
0.6957	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4538	Approved
0.6954	Remote Similarity	NPD5709	Phase 3
0.6951	Remote Similarity	NPD1243	Approved
0.6949	Remote Similarity	NPD2489	Approved
0.6949	Remote Similarity	NPD27	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