NPASS Compound

Structure

CID262189 OpenBabel06191716062D 36 40 0 0 1 0 0 0 0 0999 V2000 -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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 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 -1.7321 0.0000 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 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 1.7321 1.0000 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 -6.9282 -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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 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 2.5981 1.5000 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 2.5981 -3.5000 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 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 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 2.5981 -4.5000 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 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 6 2 0 0 0 0 3 15 1 0 0 0 0 4 5 2 0 0 0 0 4 17 1 0 0 0 0 5 23 1 0 0 0 0 6 25 1 0 0 0 0 7 16 2 0 0 0 0 7 19 1 0 0 0 0 8 16 1 0 0 0 0 8 20 2 0 0 0 0 9 15 2 0 0 0 0 9 26 1 0 0 0 0 10 18 2 0 0 0 0 10 21 1 0 0 0 0 11 18 1 0 0 0 0 11 22 2 0 0 0 0 12 17 2 0 0 0 0 12 24 1 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 14 22 1 0 0 0 0 19 29 1 0 0 0 0 20 30 1 0 0 0 0 21 31 1 0 0 0 0 22 32 1 0 0 0 0 23 24 2 0 0 0 0 23 33 1 0 0 0 0 24 34 1 0 0 0 0 25 26 2 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 17 1 1 0 0 0 27 28 1 0 0 0 0 27 36 1 0 0 0 0 28 18 1 6 0 0 0 28 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.13
Volume:	486.11
LogP:	4.077
LogD:	3.401
LogS:	-4.504
# Rotatable Bonds:	4
TPSA:	139.84
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.168
Synthetic Accessibility Score:	3.673
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.953
MDCK Permeability:	6.416154519683914e-06
Pgp-inhibitor:	0.373
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.463
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	96.10453796386719%
Volume Distribution (VD):	0.476
Pgp-substrate:	1.783984899520874%

ADMET: Metabolism

CYP1A2-inhibitor:	0.846
CYP1A2-substrate:	0.106
CYP2C19-inhibitor:	0.257
CYP2C19-substrate:	0.037
CYP2C9-inhibitor:	0.626
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.053
CYP2D6-substrate:	0.528
CYP3A4-inhibitor:	0.948
CYP3A4-substrate:	0.105

ADMET: Excretion

Clearance (CL):	10.886
Half-life (T1/2):	0.803

ADMET: Toxicity

hERG Blockers:	0.166
Human Hepatotoxicity (H-HT):	0.281
Drug-inuced Liver Injury (DILI):	0.264
AMES Toxicity:	0.187
Rat Oral Acute Toxicity:	0.228
Maximum Recommended Daily Dose:	0.914
Skin Sensitization:	0.96
Carcinogencity:	0.16
Eye Corrosion:	0.003
Eye Irritation:	0.914
Respiratory Toxicity:	0.09

Download Data

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

Natural Product: NPC262189

Natural Product ID:	NPC262189
*Common Name:**	Cassigarol E
IUPAC Name:	4-[(2R,3R)-2-(3,5-dihydroxyphenyl)-6-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]-2,3-dihydro-1,4-benzodioxin-3-yl]benzene-1,2-diol
Synonyms:	Cassigarol E
Standard InCHIKey:	PKWWKWRCCYGTHQ-DPBCGFEQSA-N
Standard InCHI:	InChI=1S/C28H22O8/c29-19-7-16(8-20(30)13-19)2-1-15-3-6-25-26(9-15)36-27(17-4-5-23(33)24(34)12-17)28(35-25)18-10-21(31)14-22(32)11-18/h1-14,27-34H/b2-1+/t27-,28-/m1/s1
SMILES:	Oc1cc(/C=C/c2ccc3c(c2)O[C@@H]([C@H](O3)c2cc(O)cc(c2)O)c2ccc(c(c2)O)O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL593139
PubChem CID:	5315729
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003495] Stilbenolignans

*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
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(01)90945-1]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[17907781]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	Eukaryota	bark	n.a.	n.a.	PMID[19646881]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24704449]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26967731]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17706	Caragana tibetica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14612	Cassia garrettiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17706	Caragana tibetica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14612	Cassia garrettiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14612	Cassia garrettiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22796	Cyperus rotundus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17706	Caragana tibetica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6645.1	Picea jezoensis var. jezoensis	Varieties	Pinaceae	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	1

Activity Type	# Activity
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	2.1	n.a.	PMID[489015]

☑ 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 NPC262189 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	498
0.1-0.2	1794
0.2-0.3	5573
0.3-0.4	12787
0.4-0.5	4519
0.5-0.6	4718
0.6-0.7	6390
0.7-0.8	4939
0.8-0.85	901
0.85-0.9	451
0.9-0.95	117
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC28440
0.9706	High Similarity	NPC171932
0.9699	High Similarity	NPC474390
0.9556	High Similarity	NPC22317
0.947	High Similarity	NPC131128
0.947	High Similarity	NPC474134
0.9429	High Similarity	NPC281549
0.9362	High Similarity	NPC211561
0.9357	High Similarity	NPC18185
0.9357	High Similarity	NPC236202
0.9357	High Similarity	NPC202742
0.9357	High Similarity	NPC262911
0.9357	High Similarity	NPC204770
0.9357	High Similarity	NPC263940
0.9357	High Similarity	NPC70409
0.9357	High Similarity	NPC58190
0.9357	High Similarity	NPC294558
0.9357	High Similarity	NPC108811
0.9357	High Similarity	NPC170103
0.9357	High Similarity	NPC82917
0.9343	High Similarity	NPC178054
0.9338	High Similarity	NPC22517
0.9328	High Similarity	NPC256307
0.9328	High Similarity	NPC170694
0.9328	High Similarity	NPC66840
0.9296	High Similarity	NPC477612
0.9291	High Similarity	NPC227516
0.9291	High Similarity	NPC20757
0.9286	High Similarity	NPC96576
0.927	High Similarity	NPC266197
0.927	High Similarity	NPC291101
0.9265	High Similarity	NPC211549
0.9259	High Similarity	NPC94750
0.9259	High Similarity	NPC474206
0.9259	High Similarity	NPC121812
0.9259	High Similarity	NPC112246
0.9259	High Similarity	NPC470356
0.9259	High Similarity	NPC112939
0.9225	High Similarity	NPC321657
0.9225	High Similarity	NPC318373
0.9197	High Similarity	NPC55947
0.9191	High Similarity	NPC306441
0.9191	High Similarity	NPC269091
0.9191	High Similarity	NPC302701
0.9191	High Similarity	NPC474639
0.9191	High Similarity	NPC230734
0.9191	High Similarity	NPC227503
0.9191	High Similarity	NPC16435
0.9179	High Similarity	NPC160991
0.9179	High Similarity	NPC470752
0.9179	High Similarity	NPC184447
0.9179	High Similarity	NPC201587
0.9179	High Similarity	NPC7903
0.9179	High Similarity	NPC253105
0.9179	High Similarity	NPC16208
0.9179	High Similarity	NPC35932
0.9143	High Similarity	NPC304894
0.9143	High Similarity	NPC15659
0.9124	High Similarity	NPC102904
0.9124	High Similarity	NPC103976
0.9124	High Similarity	NPC474282
0.9124	High Similarity	NPC107551
0.9124	High Similarity	NPC326797
0.9124	High Similarity	NPC176051
0.9118	High Similarity	NPC234333
0.9118	High Similarity	NPC47398
0.9118	High Similarity	NPC151224
0.9118	High Similarity	NPC260898
0.9118	High Similarity	NPC164787
0.9118	High Similarity	NPC61946
0.9111	High Similarity	NPC11060
0.9104	High Similarity	NPC472597
0.9104	High Similarity	NPC309787
0.9091	High Similarity	NPC473266
0.9091	High Similarity	NPC476969
0.9091	High Similarity	NPC470098
0.9091	High Similarity	NPC470826
0.9071	High Similarity	NPC173203
0.9071	High Similarity	NPC163508
0.9065	High Similarity	NPC469661
0.9051	High Similarity	NPC265433
0.9051	High Similarity	NPC162659
0.9051	High Similarity	NPC270456
0.9051	High Similarity	NPC248727
0.9044	High Similarity	NPC310854
0.9044	High Similarity	NPC317380
0.9037	High Similarity	NPC15658
0.9037	High Similarity	NPC126029
0.9037	High Similarity	NPC86655
0.9037	High Similarity	NPC219876
0.9037	High Similarity	NPC185604
0.9037	High Similarity	NPC261619
0.9037	High Similarity	NPC61477
0.9037	High Similarity	NPC127624
0.9037	High Similarity	NPC202762
0.9037	High Similarity	NPC78770
0.9034	High Similarity	NPC226809
0.9034	High Similarity	NPC226108
0.9034	High Similarity	NPC279406
0.9034	High Similarity	NPC272552
0.9034	High Similarity	NPC134911
0.9034	High Similarity	NPC322899
0.9034	High Similarity	NPC469944
0.9034	High Similarity	NPC44192
0.9034	High Similarity	NPC46283
0.903	High Similarity	NPC472338
0.9023	High Similarity	NPC72529
0.9021	High Similarity	NPC329836
0.9014	High Similarity	NPC150714
0.9014	High Similarity	NPC40222
0.9014	High Similarity	NPC95652
0.9014	High Similarity	NPC268515
0.9007	High Similarity	NPC471415
0.9007	High Similarity	NPC470097
0.9007	High Similarity	NPC114119
0.9	High Similarity	NPC189115
0.8993	High Similarity	NPC55793
0.8993	High Similarity	NPC309124
0.8993	High Similarity	NPC184797
0.8986	High Similarity	NPC48956
0.8986	High Similarity	NPC276490
0.8978	High Similarity	NPC473413
0.8973	High Similarity	NPC306267
0.8973	High Similarity	NPC224161
0.8973	High Similarity	NPC20050
0.8971	High Similarity	NPC263064
0.8971	High Similarity	NPC475840
0.8971	High Similarity	NPC229442
0.8971	High Similarity	NPC168059
0.8966	High Similarity	NPC321972
0.8966	High Similarity	NPC329343
0.8966	High Similarity	NPC324517
0.8963	High Similarity	NPC469625
0.8963	High Similarity	NPC30043
0.8963	High Similarity	NPC42760
0.8963	High Similarity	NPC470095
0.8963	High Similarity	NPC220825
0.8963	High Similarity	NPC268266
0.8963	High Similarity	NPC268342
0.8963	High Similarity	NPC470096
0.8963	High Similarity	NPC469613
0.8958	High Similarity	NPC475250
0.8955	High Similarity	NPC86030
0.8955	High Similarity	NPC3439
0.8955	High Similarity	NPC190629
0.8955	High Similarity	NPC273295
0.8955	High Similarity	NPC285339
0.8955	High Similarity	NPC476968
0.8955	High Similarity	NPC170844
0.8955	High Similarity	NPC210623
0.8955	High Similarity	NPC226788
0.8955	High Similarity	NPC218856
0.8955	High Similarity	NPC202582
0.8955	High Similarity	NPC5851
0.8955	High Similarity	NPC470258
0.8955	High Similarity	NPC222004
0.8947	High Similarity	NPC210355
0.8947	High Similarity	NPC470699
0.8929	High Similarity	NPC100482
0.8929	High Similarity	NPC277331
0.8929	High Similarity	NPC471389
0.8929	High Similarity	NPC470372
0.8921	High Similarity	NPC260741
0.8921	High Similarity	NPC473739
0.8921	High Similarity	NPC232164
0.8921	High Similarity	NPC127218
0.8921	High Similarity	NPC70682
0.8921	High Similarity	NPC319647
0.8921	High Similarity	NPC25966
0.8921	High Similarity	NPC236306
0.8921	High Similarity	NPC245207
0.8913	High Similarity	NPC470802
0.8913	High Similarity	NPC472334
0.8913	High Similarity	NPC234952
0.8913	High Similarity	NPC472336
0.8912	High Similarity	NPC157333
0.8912	High Similarity	NPC46335
0.8889	High Similarity	NPC91291
0.8889	High Similarity	NPC469612
0.8889	High Similarity	NPC469614
0.8881	High Similarity	NPC245826
0.8881	High Similarity	NPC324492
0.8881	High Similarity	NPC470213
0.8881	High Similarity	NPC317053
0.8881	High Similarity	NPC226331
0.8881	High Similarity	NPC46274
0.8881	High Similarity	NPC186843
0.8881	High Similarity	NPC474178
0.8881	High Similarity	NPC98631
0.8881	High Similarity	NPC125755
0.8881	High Similarity	NPC206615
0.8881	High Similarity	NPC252307
0.8881	High Similarity	NPC260397
0.8873	High Similarity	NPC473045
0.8873	High Similarity	NPC138227
0.8873	High Similarity	NPC469313
0.8873	High Similarity	NPC473108
0.8873	High Similarity	NPC25292
0.8873	High Similarity	NPC76176
0.8873	High Similarity	NPC168579

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 NPC262189 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	427
0.1-0.2	876
0.2-0.3	2034
0.3-0.4	2671
0.4-0.5	1570
0.5-0.6	913
0.6-0.7	533
0.7-0.8	114
0.8-0.85	9
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9037	High Similarity	NPD1613	Approved
0.9037	High Similarity	NPD1612	Clinical (unspecified phase)
0.8955	High Similarity	NPD3027	Phase 3
0.8881	High Similarity	NPD1529	Clinical (unspecified phase)
0.8806	High Similarity	NPD1530	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD4908	Phase 1
0.8345	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.828	Intermediate Similarity	NPD6166	Phase 2
0.828	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1934	Approved
0.8088	Intermediate Similarity	NPD1610	Phase 2
0.8025	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1653	Approved
0.7935	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD1548	Phase 1
0.7872	Intermediate Similarity	NPD2861	Phase 2
0.7853	Intermediate Similarity	NPD7074	Phase 3
0.7842	Intermediate Similarity	NPD2982	Phase 2
0.7842	Intermediate Similarity	NPD2983	Phase 2
0.7791	Intermediate Similarity	NPD7054	Approved
0.777	Intermediate Similarity	NPD2981	Phase 2
0.7746	Intermediate Similarity	NPD3018	Phase 2
0.7744	Intermediate Similarity	NPD7472	Approved
0.7736	Intermediate Similarity	NPD6234	Discontinued
0.773	Intermediate Similarity	NPD7228	Approved
0.7707	Intermediate Similarity	NPD2801	Approved
0.7697	Intermediate Similarity	NPD7212	Phase 2
0.7697	Intermediate Similarity	NPD7213	Phase 3
0.7669	Intermediate Similarity	NPD228	Approved
0.7651	Intermediate Similarity	NPD7266	Discontinued
0.7647	Intermediate Similarity	NPD7447	Phase 1
0.7639	Intermediate Similarity	NPD4625	Phase 3
0.7622	Intermediate Similarity	NPD3818	Discontinued
0.7619	Intermediate Similarity	NPD8053	Approved
0.7619	Intermediate Similarity	NPD8054	Approved
0.759	Intermediate Similarity	NPD6797	Phase 2
0.7589	Intermediate Similarity	NPD4749	Approved
0.7582	Intermediate Similarity	NPD1511	Approved
0.7576	Intermediate Similarity	NPD5844	Phase 1
0.7556	Intermediate Similarity	NPD5283	Phase 1
0.755	Intermediate Similarity	NPD6674	Discontinued
0.7545	Intermediate Similarity	NPD7251	Discontinued
0.7532	Intermediate Similarity	NPD37	Approved
0.7531	Intermediate Similarity	NPD7199	Phase 2
0.7531	Intermediate Similarity	NPD6959	Discontinued
0.7516	Intermediate Similarity	NPD4380	Phase 2
0.75	Intermediate Similarity	NPD3882	Suspended
0.75	Intermediate Similarity	NPD4965	Approved
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4967	Phase 2
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD4966	Approved
0.7484	Intermediate Similarity	NPD1512	Approved
0.7484	Intermediate Similarity	NPD8455	Phase 2
0.7484	Intermediate Similarity	NPD1465	Phase 2
0.7483	Intermediate Similarity	NPD3620	Phase 2
0.7483	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1558	Phase 1
0.7466	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4538	Approved
0.745	Intermediate Similarity	NPD4536	Approved
0.745	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1091	Approved
0.7439	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD3817	Phase 2
0.7434	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6584	Phase 3
0.7429	Intermediate Similarity	NPD6516	Phase 2
0.7429	Intermediate Similarity	NPD5846	Approved
0.7405	Intermediate Similarity	NPD4675	Approved
0.7405	Intermediate Similarity	NPD4678	Approved
0.74	Intermediate Similarity	NPD5588	Approved
0.74	Intermediate Similarity	NPD5960	Phase 3
0.7396	Intermediate Similarity	NPD7549	Discontinued
0.7353	Intermediate Similarity	NPD7843	Approved
0.7342	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6190	Approved
0.7338	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7097	Phase 1
0.7329	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD7157	Approved
0.7313	Intermediate Similarity	NPD2684	Approved
0.7308	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6233	Phase 2
0.7273	Intermediate Similarity	NPD3787	Discontinued
0.7273	Intermediate Similarity	NPD6232	Discontinued
0.7262	Intermediate Similarity	NPD8156	Discontinued
0.7259	Intermediate Similarity	NPD3022	Approved
0.7259	Intermediate Similarity	NPD3021	Approved
0.7256	Intermediate Similarity	NPD5494	Approved
0.7255	Intermediate Similarity	NPD1549	Phase 2
0.7248	Intermediate Similarity	NPD4060	Phase 1
0.7244	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7075	Discontinued
0.7235	Intermediate Similarity	NPD7240	Approved
0.723	Intermediate Similarity	NPD6798	Discontinued
0.723	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6583	Phase 3
0.7222	Intermediate Similarity	NPD6582	Phase 2
0.7215	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1652	Phase 2
0.7203	Intermediate Similarity	NPD3705	Approved
0.7202	Intermediate Similarity	NPD8099	Discontinued
0.7202	Intermediate Similarity	NPD8251	Approved
0.7202	Intermediate Similarity	NPD8252	Approved
0.72	Intermediate Similarity	NPD5124	Phase 1
0.72	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD6671	Approved
0.719	Intermediate Similarity	NPD3540	Phase 1
0.7186	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5058	Phase 3
0.7178	Intermediate Similarity	NPD7768	Phase 2
0.7164	Intermediate Similarity	NPD968	Approved
0.7162	Intermediate Similarity	NPD7095	Approved
0.716	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD7411	Suspended
0.7135	Intermediate Similarity	NPD6559	Discontinued
0.7134	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4005	Discontinued
0.7124	Intermediate Similarity	NPD3539	Phase 1
0.7117	Intermediate Similarity	NPD5402	Approved
0.7097	Intermediate Similarity	NPD5177	Phase 3
0.7097	Intermediate Similarity	NPD3060	Approved
0.7089	Intermediate Similarity	NPD4123	Phase 3
0.7089	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD7906	Approved
0.7086	Intermediate Similarity	NPD5735	Approved
0.7083	Intermediate Similarity	NPD422	Phase 1
0.7069	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD8651	Approved
0.7055	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD4577	Approved
0.7052	Intermediate Similarity	NPD4578	Approved
0.7051	Intermediate Similarity	NPD7466	Approved
0.7051	Intermediate Similarity	NPD6331	Phase 2
0.7051	Intermediate Similarity	NPD3750	Approved
0.7045	Intermediate Similarity	NPD1242	Phase 1
0.7045	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7037	Approved
0.7029	Intermediate Similarity	NPD4663	Approved
0.7025	Intermediate Similarity	NPD4357	Discontinued
0.7013	Intermediate Similarity	NPD6099	Approved
0.7013	Intermediate Similarity	NPD6100	Approved
0.7006	Intermediate Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD2122	Discontinued
0.6993	Remote Similarity	NPD1357	Approved
0.6987	Remote Similarity	NPD4236	Phase 3
0.6987	Remote Similarity	NPD4237	Approved
0.6987	Remote Similarity	NPD4162	Approved
0.6985	Remote Similarity	NPD290	Approved
0.698	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD5535	Approved
0.6974	Remote Similarity	NPD230	Phase 1
0.6974	Remote Similarity	NPD4340	Discontinued
0.6972	Remote Similarity	NPD5536	Phase 2
0.6968	Remote Similarity	NPD1375	Discontinued
0.6962	Remote Similarity	NPD7124	Phase 2
0.6959	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7680	Approved
0.6954	Remote Similarity	NPD8312	Approved
0.6954	Remote Similarity	NPD7310	Approved
0.6954	Remote Similarity	NPD7311	Approved
0.6954	Remote Similarity	NPD7312	Approved
0.6954	Remote Similarity	NPD7313	Approved
0.6954	Remote Similarity	NPD8313	Approved
0.6951	Remote Similarity	NPD7819	Suspended
0.6948	Remote Similarity	NPD1510	Phase 2
0.6943	Remote Similarity	NPD4110	Phase 3
0.6943	Remote Similarity	NPD4628	Phase 3
0.6943	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4535	Phase 3
0.6943	Remote Similarity	NPD3892	Phase 2
0.6937	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2235	Phase 2
0.6918	Remote Similarity	NPD2231	Phase 2
0.6914	Remote Similarity	NPD7309	Approved
0.6914	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD2796	Approved
0.6899	Remote Similarity	NPD2677	Approved
0.6899	Remote Similarity	NPD2219	Phase 1

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