NPASS Compound

Structure

NPC475250 OpenBabel07101719152D 51 54 0 0 1 0 0 0 0 0999 V2000 -1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 46 1 0 0 0 0 2 47 1 0 0 0 0 3 48 1 0 0 0 0 4 5 2 0 0 0 0 4 20 1 0 0 0 0 5 27 1 0 0 0 0 6 13 1 0 0 0 0 6 25 2 0 0 0 0 7 14 2 0 0 0 0 7 25 1 0 0 0 0 8 15 1 0 0 0 0 8 26 2 0 0 0 0 9 16 2 0 0 0 0 9 26 1 0 0 0 0 10 18 2 0 0 0 0 10 25 1 0 0 0 0 11 19 2 0 0 0 0 11 26 1 0 0 0 0 12 17 2 0 0 0 0 12 28 1 0 0 0 0 13 29 2 0 0 0 0 14 29 1 0 0 0 0 15 30 2 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 36 1 0 0 0 0 19 37 1 0 0 0 0 20 49 1 0 0 0 0 21 27 2 0 0 0 0 21 33 1 0 0 0 0 22 27 1 0 0 0 0 22 34 2 0 0 0 0 23 28 2 0 0 0 0 23 32 1 0 0 0 0 24 35 1 0 0 0 0 24 50 1 0 0 0 0 28 38 1 0 0 0 0 29 40 1 0 0 0 0 30 41 1 0 0 0 0 31 32 2 0 0 0 0 31 42 1 0 0 0 0 32 46 1 0 0 0 0 33 39 2 0 0 0 0 33 47 1 0 0 0 0 34 39 1 0 0 0 0 34 48 1 0 0 0 0 35 38 1 0 0 0 0 35 51 1 0 0 0 0 36 43 2 0 0 0 0 36 49 1 0 0 0 0 37 44 2 0 0 0 0 37 50 1 0 0 0 0 38 45 1 0 0 0 0 39 51 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	698.24
Volume:	709.537
LogP:	4.612
LogD:	4.016
LogS:	-3.497
# Rotatable Bonds:	18
TPSA:	170.44
# H-Bond Aceptor:	12
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.082
Synthetic Accessibility Score:	3.902
Fsp3:	0.179
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.107
MDCK Permeability:	1.762491956469603e-05
Pgp-inhibitor:	0.851
Pgp-substrate:	0.338
Human Intestinal Absorption (HIA):	0.36
20% Bioavailability (F20%):	0.993
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.036
Plasma Protein Binding (PPB):	101.74585723876953%
Volume Distribution (VD):	0.366
Pgp-substrate:	1.5738766193389893%

ADMET: Metabolism

CYP1A2-inhibitor:	0.145
CYP1A2-substrate:	0.641
CYP2C19-inhibitor:	0.866
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.898
CYP2C9-substrate:	0.981
CYP2D6-inhibitor:	0.397
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.823
CYP3A4-substrate:	0.853

ADMET: Excretion

Clearance (CL):	7.324
Half-life (T1/2):	0.918

ADMET: Toxicity

hERG Blockers:	0.456
Human Hepatotoxicity (H-HT):	0.064
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.363
Rat Oral Acute Toxicity:	0.055
Maximum Recommended Daily Dose:	0.848
Skin Sensitization:	0.972
Carcinogencity:	0.256
Eye Corrosion:	0.003
Eye Irritation:	0.037
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC475250

Natural Product ID:	NPC475250
*Common Name:**	Dadahol A
IUPAC Name:	[(E)-3-[4-[1-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxypropan-2-yl]oxy-3,5-dimethoxyphenyl]prop-2-enyl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:
Standard InCHIKey:	IKHAPHPJWABCCU-WGSZPKJISA-N
Standard InCHI:	InChI=1S/C39H38O12/c1-46-32-23-28(12-17-31(32)42)38(45)35(24-50-37(44)19-11-26-8-15-30(41)16-9-26)51-39-33(47-2)21-27(22-34(39)48-3)5-4-20-49-36(43)18-10-25-6-13-29(40)14-7-25/h4-19,21-23,35,38,40-42,45H,20,24H2,1-3H3/b5-4+,18-10+,19-11+
SMILES:	COC1=CC(=CC(=C1OC(COC(=O)C=CC2=CC=C(C=C2)O)C(C3=CC(=C(C=C3)O)OC)O)OC)C=CCOC(=O)C=CC4=CC=C(C=C4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501943
PubChem CID:	10908643
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds

*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
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	bark and twigs	Tewah, Central Kalimantan, Indonesia (N 38 57.003; W 094 44.767)	1999-Oct	PMID[11858749]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10498	Artocarpus dadah	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10498	Artocarpus dadah	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
IC50	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[463147]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[463147]

☑ 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 NPC475250 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	338
0.1-0.2	1508
0.2-0.3	4141
0.3-0.4	10170
0.4-0.5	8204
0.5-0.6	3956
0.6-0.7	6142
0.7-0.8	6722
0.8-0.85	1137
0.85-0.9	333
0.9-0.95	39
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9716	High Similarity	NPC473909
0.9716	High Similarity	NPC274960
0.9716	High Similarity	NPC143120
0.9338	High Similarity	NPC476373
0.9333	High Similarity	NPC125495
0.9247	High Similarity	NPC102934
0.9247	High Similarity	NPC476348
0.9247	High Similarity	NPC252402
0.9247	High Similarity	NPC187398
0.9241	High Similarity	NPC268515
0.9241	High Similarity	NPC40222
0.9216	High Similarity	NPC476372
0.9216	High Similarity	NPC476371
0.9184	High Similarity	NPC106138
0.9178	High Similarity	NPC476347
0.9149	High Similarity	NPC471719
0.9128	High Similarity	NPC163598
0.9128	High Similarity	NPC120774
0.9128	High Similarity	NPC264875
0.9122	High Similarity	NPC120426
0.9122	High Similarity	NPC294522
0.9122	High Similarity	NPC205727
0.9122	High Similarity	NPC21184
0.9097	High Similarity	NPC193722
0.9097	High Similarity	NPC278469
0.9091	High Similarity	NPC267291
0.9085	High Similarity	NPC126206
0.9085	High Similarity	NPC474390
0.9079	High Similarity	NPC470827
0.9067	High Similarity	NPC115203
0.9054	High Similarity	NPC176903
0.9054	High Similarity	NPC30688
0.9038	High Similarity	NPC59516
0.9028	High Similarity	NPC83375
0.9028	High Similarity	NPC224876
0.902	High Similarity	NPC470828
0.9014	High Similarity	NPC471664
0.9014	High Similarity	NPC471665
0.9007	High Similarity	NPC309744
0.9007	High Similarity	NPC469888
0.9007	High Similarity	NPC135127
0.9	High Similarity	NPC472612
0.9	High Similarity	NPC289967
0.9	High Similarity	NPC472611
0.8958	High Similarity	NPC106055
0.8958	High Similarity	NPC291101
0.8958	High Similarity	NPC266197
0.8958	High Similarity	NPC262189
0.8958	High Similarity	NPC110699
0.8958	High Similarity	NPC22317
0.894	High Similarity	NPC475141
0.8926	High Similarity	NPC470826
0.8926	High Similarity	NPC473266
0.8926	High Similarity	NPC470098
0.8919	High Similarity	NPC15577
0.8889	High Similarity	NPC22517
0.8882	High Similarity	NPC473736
0.8873	High Similarity	NPC170694
0.8873	High Similarity	NPC111635
0.8867	High Similarity	NPC477612
0.8865	High Similarity	NPC16208
0.8865	High Similarity	NPC35932
0.8865	High Similarity	NPC184447
0.8865	High Similarity	NPC160991
0.8865	High Similarity	NPC7903
0.8859	High Similarity	NPC281549
0.8859	High Similarity	NPC478237
0.8846	High Similarity	NPC12326
0.8844	High Similarity	NPC28440
0.8844	High Similarity	NPC171932
0.8836	High Similarity	NPC67467
0.8816	High Similarity	NPC470769
0.8816	High Similarity	NPC150442
0.8808	High Similarity	NPC7145
0.8808	High Similarity	NPC125823
0.8808	High Similarity	NPC85192
0.8808	High Similarity	NPC143480
0.8808	High Similarity	NPC329343
0.8808	High Similarity	NPC321972
0.8808	High Similarity	NPC324517
0.88	High Similarity	NPC283839
0.88	High Similarity	NPC90896
0.8794	High Similarity	NPC470096
0.8794	High Similarity	NPC469625
0.8794	High Similarity	NPC469613
0.8794	High Similarity	NPC30043
0.8794	High Similarity	NPC470095
0.8794	High Similarity	NPC472597
0.8784	High Similarity	NPC252292
0.8784	High Similarity	NPC34927
0.8784	High Similarity	NPC100998
0.8784	High Similarity	NPC34587
0.8784	High Similarity	NPC476382
0.8782	High Similarity	NPC149873
0.8782	High Similarity	NPC7191
0.8776	High Similarity	NPC478239
0.8767	High Similarity	NPC470372
0.8766	High Similarity	NPC11411
0.8766	High Similarity	NPC473275
0.8766	High Similarity	NPC470896
0.8758	High Similarity	NPC476374
0.8758	High Similarity	NPC8712
0.875	High Similarity	NPC169404
0.875	High Similarity	NPC53587
0.875	High Similarity	NPC476434
0.875	High Similarity	NPC476365
0.875	High Similarity	NPC478268
0.875	High Similarity	NPC176186
0.875	High Similarity	NPC180768
0.875	High Similarity	NPC120852
0.875	High Similarity	NPC75695
0.8742	High Similarity	NPC476871
0.8741	High Similarity	NPC249791
0.8741	High Similarity	NPC237594
0.8741	High Similarity	NPC119060
0.8741	High Similarity	NPC310854
0.8741	High Similarity	NPC476387
0.8733	High Similarity	NPC28651
0.8733	High Similarity	NPC300262
0.8733	High Similarity	NPC192763
0.8733	High Similarity	NPC80732
0.8733	High Similarity	NPC210611
0.8733	High Similarity	NPC199311
0.8733	High Similarity	NPC261122
0.8733	High Similarity	NPC93924
0.8733	High Similarity	NPC201148
0.8733	High Similarity	NPC215095
0.8733	High Similarity	NPC3460
0.8732	High Similarity	NPC131128
0.8732	High Similarity	NPC5423
0.8732	High Similarity	NPC245120
0.8732	High Similarity	NPC474134
0.8732	High Similarity	NPC470752
0.8725	High Similarity	NPC476865
0.8725	High Similarity	NPC199928
0.8723	High Similarity	NPC472338
0.8723	High Similarity	NPC469612
0.8723	High Similarity	NPC307042
0.8723	High Similarity	NPC79184
0.8723	High Similarity	NPC469614
0.8718	High Similarity	NPC53889
0.8716	High Similarity	NPC470097
0.8716	High Similarity	NPC471415
0.8716	High Similarity	NPC114119
0.8707	High Similarity	NPC157816
0.8707	High Similarity	NPC469559
0.8707	High Similarity	NPC140502
0.8696	High Similarity	NPC476370
0.8693	High Similarity	NPC149735
0.8693	High Similarity	NPC146277
0.8693	High Similarity	NPC474656
0.8693	High Similarity	NPC19380
0.8684	High Similarity	NPC300329
0.8681	High Similarity	NPC214729
0.8675	High Similarity	NPC94871
0.8675	High Similarity	NPC470933
0.8675	High Similarity	NPC471062
0.8675	High Similarity	NPC473427
0.8675	High Similarity	NPC306890
0.8675	High Similarity	NPC318373
0.8675	High Similarity	NPC211561
0.8675	High Similarity	NPC321657
0.8675	High Similarity	NPC259347
0.8675	High Similarity	NPC476386
0.8675	High Similarity	NPC476398
0.8671	High Similarity	NPC36490
0.8667	High Similarity	NPC328567
0.8667	High Similarity	NPC320671
0.8667	High Similarity	NPC232992
0.8667	High Similarity	NPC178129
0.8667	High Similarity	NPC327412
0.8667	High Similarity	NPC320970
0.8662	High Similarity	NPC309787
0.8658	High Similarity	NPC476868
0.8658	High Similarity	NPC476864
0.8658	High Similarity	NPC476869
0.8658	High Similarity	NPC476866
0.8654	High Similarity	NPC87317
0.8654	High Similarity	NPC478269
0.8652	High Similarity	NPC470258
0.8652	High Similarity	NPC190629
0.8652	High Similarity	NPC202582
0.8652	High Similarity	NPC48315
0.8652	High Similarity	NPC226788
0.8652	High Similarity	NPC222004
0.8652	High Similarity	NPC210623
0.8652	High Similarity	NPC273295
0.8652	High Similarity	NPC83062
0.8652	High Similarity	NPC285339
0.8652	High Similarity	NPC3439
0.8652	High Similarity	NPC218856
0.8649	High Similarity	NPC110067
0.8649	High Similarity	NPC91492
0.8649	High Similarity	NPC34245
0.8649	High Similarity	NPC7439
0.8649	High Similarity	NPC256555
0.8639	High Similarity	NPC186406
0.8639	High Similarity	NPC178054
0.8636	High Similarity	NPC268484
0.863	High Similarity	NPC55947

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 NPC475250 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	292
0.1-0.2	879
0.2-0.3	1835
0.3-0.4	2699
0.4-0.5	1738
0.5-0.6	976
0.6-0.7	587
0.7-0.8	135
0.8-0.85	7
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8526	High Similarity	NPD4868	Clinical (unspecified phase)
0.8521	High Similarity	NPD3027	Phase 3
0.8431	Intermediate Similarity	NPD1653	Approved
0.8378	Intermediate Similarity	NPD7266	Discontinued
0.8354	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD1613	Approved
0.8345	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD6166	Phase 2
0.8069	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.8012	Intermediate Similarity	NPD7054	Approved
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1934	Approved
0.7964	Intermediate Similarity	NPD7472	Approved
0.7964	Intermediate Similarity	NPD7074	Phase 3
0.7922	Intermediate Similarity	NPD6190	Approved
0.7888	Intermediate Similarity	NPD3817	Phase 2
0.7853	Intermediate Similarity	NPD6234	Discontinued
0.7844	Intermediate Similarity	NPD7228	Approved
0.7844	Intermediate Similarity	NPD3818	Discontinued
0.784	Intermediate Similarity	NPD7768	Phase 2
0.7826	Intermediate Similarity	NPD2801	Approved
0.7826	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7808	Phase 3
0.7823	Intermediate Similarity	NPD4908	Phase 1
0.7765	Intermediate Similarity	NPD7251	Discontinued
0.7764	Intermediate Similarity	NPD37	Approved
0.7758	Intermediate Similarity	NPD7199	Phase 2
0.7758	Intermediate Similarity	NPD8127	Discontinued
0.773	Intermediate Similarity	NPD3882	Suspended
0.773	Intermediate Similarity	NPD4967	Phase 2
0.773	Intermediate Similarity	NPD4966	Approved
0.773	Intermediate Similarity	NPD4965	Approved
0.7724	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1465	Phase 2
0.7706	Intermediate Similarity	NPD6797	Phase 2
0.7683	Intermediate Similarity	NPD7075	Discontinued
0.7677	Intermediate Similarity	NPD1652	Phase 2
0.7673	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD5402	Approved
0.7616	Intermediate Similarity	NPD7549	Discontinued
0.7607	Intermediate Similarity	NPD8455	Phase 2
0.7605	Intermediate Similarity	NPD6232	Discontinued
0.76	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1511	Approved
0.7595	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD422	Phase 1
0.7576	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7473	Discontinued
0.7566	Intermediate Similarity	NPD5124	Phase 1
0.7566	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD230	Phase 1
0.7562	Intermediate Similarity	NPD5403	Approved
0.756	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD7685	Pre-registration
0.7557	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD6233	Phase 2
0.7531	Intermediate Similarity	NPD4380	Phase 2
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7515	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7819	Suspended
0.75	Intermediate Similarity	NPD1512	Approved
0.7485	Intermediate Similarity	NPD7411	Suspended
0.7483	Intermediate Similarity	NPD2982	Phase 2
0.7483	Intermediate Similarity	NPD2983	Phase 2
0.7457	Intermediate Similarity	NPD6559	Discontinued
0.7455	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6801	Discontinued
0.7438	Intermediate Similarity	NPD5401	Approved
0.7431	Intermediate Similarity	NPD1548	Phase 1
0.7417	Intermediate Similarity	NPD7095	Approved
0.7415	Intermediate Similarity	NPD2981	Phase 2
0.7405	Intermediate Similarity	NPD3750	Approved
0.7405	Intermediate Similarity	NPD8166	Discontinued
0.74	Intermediate Similarity	NPD3018	Phase 2
0.7386	Intermediate Similarity	NPD4060	Phase 1
0.7384	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD6799	Approved
0.7371	Intermediate Similarity	NPD8313	Approved
0.7371	Intermediate Similarity	NPD8312	Approved
0.7368	Intermediate Similarity	NPD6798	Discontinued
0.7356	Intermediate Similarity	NPD7240	Approved
0.7355	Intermediate Similarity	NPD7097	Phase 1
0.7347	Intermediate Similarity	NPD1610	Phase 2
0.7342	Intermediate Similarity	NPD6674	Discontinued
0.7338	Intermediate Similarity	NPD4340	Discontinued
0.7337	Intermediate Similarity	NPD6959	Discontinued
0.7305	Intermediate Similarity	NPD228	Approved
0.7296	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5494	Approved
0.7267	Intermediate Similarity	NPD4357	Discontinued
0.7257	Intermediate Similarity	NPD7039	Approved
0.7257	Intermediate Similarity	NPD7038	Approved
0.7254	Intermediate Similarity	NPD7843	Approved
0.7241	Intermediate Similarity	NPD5536	Phase 2
0.7233	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD8053	Approved
0.7232	Intermediate Similarity	NPD8054	Approved
0.7222	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3686	Approved
0.7195	Intermediate Similarity	NPD3687	Approved
0.7179	Intermediate Similarity	NPD6653	Approved
0.7178	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2861	Phase 2
0.717	Intermediate Similarity	NPD1549	Phase 2
0.7166	Intermediate Similarity	NPD7680	Approved
0.7162	Intermediate Similarity	NPD3496	Discontinued
0.7161	Intermediate Similarity	NPD3620	Phase 2
0.7161	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1558	Phase 1
0.716	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6971	Discontinued
0.7152	Intermediate Similarity	NPD1551	Phase 2
0.7143	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5535	Approved
0.7126	Intermediate Similarity	NPD3751	Discontinued
0.7117	Intermediate Similarity	NPD7447	Phase 1
0.7117	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD6355	Discontinued
0.7115	Intermediate Similarity	NPD447	Suspended
0.7114	Intermediate Similarity	NPD1091	Approved
0.7108	Intermediate Similarity	NPD4675	Approved
0.7108	Intermediate Similarity	NPD6599	Discontinued
0.7108	Intermediate Similarity	NPD4678	Approved
0.7107	Intermediate Similarity	NPD5762	Approved
0.7107	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5763	Approved
0.7103	Intermediate Similarity	NPD7157	Approved
0.7093	Intermediate Similarity	NPD3787	Discontinued
0.7089	Intermediate Similarity	NPD3748	Approved
0.7088	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3225	Approved
0.7083	Intermediate Similarity	NPD5283	Phase 1
0.7081	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD4110	Phase 3
0.7078	Intermediate Similarity	NPD4625	Phase 3
0.7073	Intermediate Similarity	NPD6273	Approved
0.7066	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3749	Approved
0.7055	Intermediate Similarity	NPD7212	Phase 2
0.7055	Intermediate Similarity	NPD7213	Phase 3
0.7051	Intermediate Similarity	NPD4140	Approved
0.7048	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD2935	Discontinued
0.7044	Intermediate Similarity	NPD2796	Approved
0.7043	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5353	Approved
0.7039	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4536	Approved
0.7025	Intermediate Similarity	NPD4538	Approved
0.7025	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1358	Approved
0.702	Intermediate Similarity	NPD4749	Approved
0.7019	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3705	Approved
0.6994	Remote Similarity	NPD7229	Phase 3
0.6993	Remote Similarity	NPD6584	Phase 3
0.6987	Remote Similarity	NPD4062	Phase 3
0.6981	Remote Similarity	NPD1510	Phase 2
0.6981	Remote Similarity	NPD7033	Discontinued
0.698	Remote Similarity	NPD6516	Phase 2
0.698	Remote Similarity	NPD5846	Approved
0.6974	Remote Similarity	NPD8651	Approved
0.6972	Remote Similarity	NPD2684	Approved
0.6964	Remote Similarity	NPD6386	Approved
0.6964	Remote Similarity	NPD6385	Approved
0.6957	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5242	Approved
0.6948	Remote Similarity	NPD9494	Approved
0.6933	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD2797	Approved
0.6923	Remote Similarity	NPD6841	Approved
0.6923	Remote Similarity	NPD6843	Phase 3
0.6923	Remote Similarity	NPD7945	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6842	Approved
0.6919	Remote Similarity	NPD919	Approved
0.6914	Remote Similarity	NPD3060	Approved
0.6913	Remote Similarity	NPD1357	Approved
0.6909	Remote Similarity	NPD3536	Discontinued
0.6903	Remote Similarity	NPD6832	Phase 2
0.6899	Remote Similarity	NPD1933	Approved
0.6899	Remote Similarity	NPD5735	Approved
0.6894	Remote Similarity	NPD3540	Phase 1
0.6893	Remote Similarity	NPD8156	Discontinued
0.6891	Remote Similarity	NPD8151	Discontinued
0.689	Remote Similarity	NPD7440	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