NPASS Compound

Structure

NPC474660 OpenBabel07101718322D 27 29 0 0 0 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 -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 3.4641 -3.0000 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 -2.5981 -0.5000 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 -2.5981 -1.5000 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 2.5981 1.5000 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 -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 0.0000 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 -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 0.0000 -2.0000 0.0000 C 0 0 0 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 -3.4641 1.0000 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 0.0000 -3.0000 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 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 11 1 0 0 0 0 4 25 1 0 0 0 0 5 9 2 0 0 0 0 5 13 1 0 0 0 0 6 9 1 0 0 0 0 6 15 2 0 0 0 0 7 12 2 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 10 21 2 0 0 0 0 10 26 1 0 0 0 0 11 22 2 0 0 0 0 11 27 1 0 0 0 0 12 25 1 0 0 0 0 13 17 2 0 0 0 0 13 19 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 17 1 0 0 0 0 15 26 1 0 0 0 0 16 18 1 0 0 0 0 16 27 1 0 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 19 23 2 0 0 0 0 20 24 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	368.09
Volume:	363.974
LogP:	3.08
LogD:	2.273
LogS:	-6.126
# Rotatable Bonds:	5
TPSA:	95.97
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	2.445
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.01
MDCK Permeability:	5.039520692662336e-05
Pgp-inhibitor:	0.917
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.03
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.696

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.321
Plasma Protein Binding (PPB):	84.1817626953125%
Volume Distribution (VD):	0.946
Pgp-substrate:	15.71175479888916%

ADMET: Metabolism

CYP1A2-inhibitor:	0.895
CYP1A2-substrate:	0.231
CYP2C19-inhibitor:	0.529
CYP2C19-substrate:	0.077
CYP2C9-inhibitor:	0.74
CYP2C9-substrate:	0.692
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.266
CYP3A4-inhibitor:	0.712
CYP3A4-substrate:	0.178

ADMET: Excretion

Clearance (CL):	1.822
Half-life (T1/2):	0.243

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.026
Drug-inuced Liver Injury (DILI):	0.824
AMES Toxicity:	0.731
Rat Oral Acute Toxicity:	0.563
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.396
Carcinogencity:	0.255
Eye Corrosion:	0.004
Eye Irritation:	0.954
Respiratory Toxicity:	0.327

Download Data

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

Natural Product: NPC474660

Natural Product ID:	NPC474660
*Common Name:**	Physcion Diacetate
IUPAC Name:	(8-acetyloxy-6-methoxy-3-methyl-9,10-dioxoanthracen-1-yl) acetate
Synonyms:	Physcion Diacetate
Standard InCHIKey:	NZOKPGYOGJBULF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C20H16O7/c1-9-5-13-17(15(6-9)26-10(2)21)20(24)18-14(19(13)23)7-12(25-4)8-16(18)27-11(3)22/h5-8H,1-4H3
SMILES:	CC1=CC2=C(C(=C1)OC(=O)C)C(=O)C3=C(C2=O)C=C(C=C3OC(=O)C)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL478752
PubChem CID:	15081093
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones

*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
NPO33118	Rhamnus	Genus	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350094]

☑ 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
CELL-LINE	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	76.5	%	PMID[478296]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	90.3	%	PMID[478296]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	89.4	%	PMID[478296]
NPT20967	CELL-LINE	Platelet	n.a.	Activity	=	93.9	%	PMID[478296]

☑ 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 NPC474660 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	462
0.1-0.2	1780
0.2-0.3	4258
0.3-0.4	9833
0.4-0.5	8443
0.5-0.6	3820
0.6-0.7	5771
0.7-0.8	5656
0.8-0.85	2290
0.85-0.9	343
0.9-0.95	38
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC473466
0.9583	High Similarity	NPC473927
0.951	High Similarity	NPC167663
0.9379	High Similarity	NPC49282
0.9346	High Similarity	NPC108767
0.9329	High Similarity	NPC154683
0.9329	High Similarity	NPC40356
0.931	High Similarity	NPC189650
0.9272	High Similarity	NPC146211
0.9257	High Similarity	NPC291049
0.9257	High Similarity	NPC233267
0.9189	High Similarity	NPC105415
0.9133	High Similarity	NPC133856
0.9122	High Similarity	NPC245584
0.9122	High Similarity	NPC118027
0.9122	High Similarity	NPC289042
0.9122	High Similarity	NPC56433
0.9122	High Similarity	NPC126767
0.9122	High Similarity	NPC190648
0.9122	High Similarity	NPC312929
0.9085	High Similarity	NPC263483
0.9073	High Similarity	NPC273483
0.9067	High Similarity	NPC470568
0.906	High Similarity	NPC172329
0.906	High Similarity	NPC2569
0.906	High Similarity	NPC472056
0.9051	High Similarity	NPC49487
0.9051	High Similarity	NPC99613
0.9045	High Similarity	NPC29160
0.9041	High Similarity	NPC24075
0.9013	High Similarity	NPC214632
0.9007	High Similarity	NPC149526
0.9007	High Similarity	NPC478148
0.9007	High Similarity	NPC470569
0.9007	High Similarity	NPC189773
0.9007	High Similarity	NPC474417
0.9	High Similarity	NPC158338
0.9	High Similarity	NPC288036
0.9	High Similarity	NPC97028
0.9	High Similarity	NPC97029
0.9	High Similarity	NPC100985
0.9	High Similarity	NPC65589
0.8987	High Similarity	NPC76647
0.8987	High Similarity	NPC234331
0.8986	High Similarity	NPC134621
0.898	High Similarity	NPC215451
0.898	High Similarity	NPC277369
0.8973	High Similarity	NPC171094
0.8958	High Similarity	NPC268081
0.8954	High Similarity	NPC89625
0.8954	High Similarity	NPC149618
0.8947	High Similarity	NPC217447
0.894	High Similarity	NPC255641
0.894	High Similarity	NPC470107
0.894	High Similarity	NPC295036
0.894	High Similarity	NPC290954
0.894	High Similarity	NPC147735
0.894	High Similarity	NPC294646
0.8938	High Similarity	NPC158226
0.8933	High Similarity	NPC27221
0.8933	High Similarity	NPC256672
0.8933	High Similarity	NPC7025
0.8931	High Similarity	NPC165979
0.8931	High Similarity	NPC163130
0.8926	High Similarity	NPC225173
0.8926	High Similarity	NPC163846
0.8926	High Similarity	NPC237208
0.8924	High Similarity	NPC30027
0.8919	High Similarity	NPC95123
0.8919	High Similarity	NPC19896
0.8919	High Similarity	NPC66404
0.8904	High Similarity	NPC109007
0.8904	High Similarity	NPC136095
0.8904	High Similarity	NPC472515
0.8904	High Similarity	NPC473209
0.8897	High Similarity	NPC103001
0.8897	High Similarity	NPC253616
0.8889	High Similarity	NPC329844
0.8882	High Similarity	NPC232645
0.8882	High Similarity	NPC72958
0.8874	High Similarity	NPC70764
0.8874	High Similarity	NPC10027
0.8874	High Similarity	NPC65775
0.8867	High Similarity	NPC22005
0.8867	High Similarity	NPC7943
0.8867	High Similarity	NPC125801
0.8867	High Similarity	NPC34802
0.8867	High Similarity	NPC123202
0.8867	High Similarity	NPC12305
0.8859	High Similarity	NPC29577
0.8851	High Similarity	NPC471643
0.8851	High Similarity	NPC471639
0.8846	High Similarity	NPC143050
0.8839	High Similarity	NPC201127
0.8836	High Similarity	NPC36414
0.8831	High Similarity	NPC226656
0.8831	High Similarity	NPC66508
0.8824	High Similarity	NPC87708
0.8824	High Similarity	NPC175978
0.8816	High Similarity	NPC325983
0.8816	High Similarity	NPC158866
0.8816	High Similarity	NPC309979
0.8816	High Similarity	NPC307780
0.8816	High Similarity	NPC150928
0.8816	High Similarity	NPC60413
0.8816	High Similarity	NPC202595
0.8808	High Similarity	NPC37139
0.8805	High Similarity	NPC477835
0.8805	High Similarity	NPC125465
0.88	High Similarity	NPC267509
0.88	High Similarity	NPC470570
0.8792	High Similarity	NPC470932
0.8784	High Similarity	NPC471644
0.8784	High Similarity	NPC105648
0.8784	High Similarity	NPC471640
0.8774	High Similarity	NPC4547
0.8774	High Similarity	NPC474983
0.8774	High Similarity	NPC180924
0.8766	High Similarity	NPC472799
0.8766	High Similarity	NPC208806
0.8766	High Similarity	NPC107109
0.8766	High Similarity	NPC210942
0.8766	High Similarity	NPC169990
0.8758	High Similarity	NPC39819
0.8758	High Similarity	NPC258249
0.875	High Similarity	NPC6923
0.875	High Similarity	NPC474648
0.875	High Similarity	NPC329933
0.875	High Similarity	NPC1249
0.8733	High Similarity	NPC32470
0.8733	High Similarity	NPC34482
0.8726	High Similarity	NPC470810
0.8725	High Similarity	NPC84266
0.8725	High Similarity	NPC310340
0.8718	High Similarity	NPC212967
0.8718	High Similarity	NPC96342
0.8718	High Similarity	NPC164110
0.8718	High Similarity	NPC199463
0.8718	High Similarity	NPC246647
0.8718	High Similarity	NPC37543
0.8716	High Similarity	NPC220106
0.8712	High Similarity	NPC68381
0.8699	High Similarity	NPC472516
0.8699	High Similarity	NPC254741
0.8699	High Similarity	NPC161196
0.8693	High Similarity	NPC205766
0.8693	High Similarity	NPC227122
0.8693	High Similarity	NPC119929
0.8684	High Similarity	NPC183236
0.8679	High Similarity	NPC474350
0.8675	High Similarity	NPC25844
0.8675	High Similarity	NPC196114
0.8675	High Similarity	NPC470322
0.8675	High Similarity	NPC154217
0.8667	High Similarity	NPC193703
0.8667	High Similarity	NPC21599
0.8667	High Similarity	NPC48762
0.8667	High Similarity	NPC184702
0.8662	High Similarity	NPC324736
0.8662	High Similarity	NPC474373
0.8658	High Similarity	NPC250755
0.8658	High Similarity	NPC94076
0.8658	High Similarity	NPC182255
0.8658	High Similarity	NPC297985
0.8658	High Similarity	NPC49108
0.8654	High Similarity	NPC14561
0.8654	High Similarity	NPC472050
0.8654	High Similarity	NPC5379
0.8654	High Similarity	NPC77807
0.8649	High Similarity	NPC11566
0.8649	High Similarity	NPC165172
0.8649	High Similarity	NPC472523
0.8645	High Similarity	NPC135522
0.8645	High Similarity	NPC186507
0.8645	High Similarity	NPC477691
0.8642	High Similarity	NPC109827
0.8642	High Similarity	NPC124470
0.8639	High Similarity	NPC259685
0.8639	High Similarity	NPC38153
0.8636	High Similarity	NPC474663
0.8627	High Similarity	NPC266499
0.8621	High Similarity	NPC292998
0.8618	High Similarity	NPC52106
0.8609	High Similarity	NPC1886
0.8609	High Similarity	NPC469953
0.8609	High Similarity	NPC311741
0.8609	High Similarity	NPC196137
0.8609	High Similarity	NPC312789
0.8609	High Similarity	NPC171656
0.8609	High Similarity	NPC179970
0.8609	High Similarity	NPC234629
0.8608	High Similarity	NPC472052
0.8608	High Similarity	NPC260296
0.8608	High Similarity	NPC470342
0.8608	High Similarity	NPC472060
0.8608	High Similarity	NPC186325
0.8608	High Similarity	NPC115432
0.86	High Similarity	NPC36181
0.86	High Similarity	NPC472006
0.8599	High Similarity	NPC44199

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 NPC474660 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	1012
0.2-0.3	1671
0.3-0.4	2632
0.4-0.5	1853
0.5-0.6	1013
0.6-0.7	368
0.7-0.8	157
0.8-0.85	40
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9013	High Similarity	NPD7819	Suspended
0.875	High Similarity	NPD3226	Approved
0.8616	High Similarity	NPD6232	Discontinued
0.8571	High Similarity	NPD7473	Discontinued
0.8571	High Similarity	NPD2796	Approved
0.8523	High Similarity	NPD1243	Approved
0.8516	High Similarity	NPD7411	Suspended
0.8503	High Similarity	NPD3748	Approved
0.8487	Intermediate Similarity	NPD2534	Approved
0.8487	Intermediate Similarity	NPD2533	Approved
0.8487	Intermediate Similarity	NPD2532	Approved
0.8452	Intermediate Similarity	NPD6599	Discontinued
0.8438	Intermediate Similarity	NPD6959	Discontinued
0.8408	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD2346	Discontinued
0.8378	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8377	Intermediate Similarity	NPD920	Approved
0.8366	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD3749	Approved
0.8354	Intermediate Similarity	NPD5844	Phase 1
0.8333	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8301	Intermediate Similarity	NPD6799	Approved
0.8261	Intermediate Similarity	NPD5494	Approved
0.825	Intermediate Similarity	NPD7075	Discontinued
0.8247	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD6801	Discontinued
0.8224	Intermediate Similarity	NPD3750	Approved
0.8187	Intermediate Similarity	NPD7768	Phase 2
0.8176	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD2799	Discontinued
0.8125	Intermediate Similarity	NPD3817	Phase 2
0.8125	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD1607	Approved
0.8092	Intermediate Similarity	NPD1549	Phase 2
0.8086	Intermediate Similarity	NPD919	Approved
0.8026	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD1510	Phase 2
0.7987	Intermediate Similarity	NPD1240	Approved
0.7963	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1551	Phase 2
0.7961	Intermediate Similarity	NPD2935	Discontinued
0.7959	Intermediate Similarity	NPD6832	Phase 2
0.795	Intermediate Similarity	NPD2801	Approved
0.7911	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3926	Phase 2
0.7888	Intermediate Similarity	NPD1934	Approved
0.7875	Intermediate Similarity	NPD4380	Phase 2
0.7871	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD3882	Suspended
0.7852	Intermediate Similarity	NPD2313	Discontinued
0.7852	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD1465	Phase 2
0.7834	Intermediate Similarity	NPD1511	Approved
0.7834	Intermediate Similarity	NPD7390	Discontinued
0.7831	Intermediate Similarity	NPD5711	Approved
0.7831	Intermediate Similarity	NPD5710	Approved
0.7824	Intermediate Similarity	NPD5953	Discontinued
0.7815	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2800	Approved
0.7792	Intermediate Similarity	NPD1471	Phase 3
0.7791	Intermediate Similarity	NPD5402	Approved
0.7784	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7756	Intermediate Similarity	NPD4628	Phase 3
0.7751	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD4307	Phase 2
0.7736	Intermediate Similarity	NPD1512	Approved
0.7727	Intermediate Similarity	NPD6100	Approved
0.7727	Intermediate Similarity	NPD5406	Approved
0.7727	Intermediate Similarity	NPD5408	Approved
0.7727	Intermediate Similarity	NPD5404	Approved
0.7727	Intermediate Similarity	NPD5405	Approved
0.7727	Intermediate Similarity	NPD6099	Approved
0.7725	Intermediate Similarity	NPD7229	Phase 3
0.7697	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD5403	Approved
0.7673	Intermediate Similarity	NPD5401	Approved
0.7665	Intermediate Similarity	NPD1247	Approved
0.7647	Intermediate Similarity	NPD3818	Discontinued
0.7643	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD7003	Approved
0.7635	Intermediate Similarity	NPD3267	Approved
0.7635	Intermediate Similarity	NPD3266	Approved
0.7633	Intermediate Similarity	NPD6166	Phase 2
0.7633	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6273	Approved
0.7603	Intermediate Similarity	NPD1281	Approved
0.7602	Intermediate Similarity	NPD7286	Phase 2
0.7586	Intermediate Similarity	NPD17	Approved
0.7586	Intermediate Similarity	NPD8313	Approved
0.7586	Intermediate Similarity	NPD8312	Approved
0.7571	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD8032	Phase 2
0.7564	Intermediate Similarity	NPD2344	Approved
0.7562	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD3972	Approved
0.7548	Intermediate Similarity	NPD4308	Phase 3
0.7544	Intermediate Similarity	NPD7177	Discontinued
0.7527	Intermediate Similarity	NPD8285	Discontinued
0.7517	Intermediate Similarity	NPD5691	Approved
0.7517	Intermediate Similarity	NPD1470	Approved
0.7517	Intermediate Similarity	NPD1203	Approved
0.7517	Intermediate Similarity	NPD1651	Approved
0.7516	Intermediate Similarity	NPD2979	Phase 3
0.7514	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD411	Approved
0.75	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3268	Approved
0.7485	Intermediate Similarity	NPD7458	Discontinued
0.7483	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD4288	Approved
0.7468	Intermediate Similarity	NPD1933	Approved
0.7467	Intermediate Similarity	NPD2798	Approved
0.7457	Intermediate Similarity	NPD7074	Phase 3
0.7456	Intermediate Similarity	NPD7199	Phase 2
0.7455	Intermediate Similarity	NPD37	Approved
0.745	Intermediate Similarity	NPD1283	Approved
0.7447	Intermediate Similarity	NPD8151	Discontinued
0.7434	Intermediate Similarity	NPD4625	Phase 3
0.7432	Intermediate Similarity	NPD9717	Approved
0.7432	Intermediate Similarity	NPD1608	Approved
0.7429	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4965	Approved
0.7425	Intermediate Similarity	NPD4967	Phase 2
0.7425	Intermediate Similarity	NPD4966	Approved
0.7419	Intermediate Similarity	NPD6651	Approved
0.74	Intermediate Similarity	NPD2797	Approved
0.7399	Intermediate Similarity	NPD7054	Approved
0.7389	Intermediate Similarity	NPD2438	Suspended
0.7386	Intermediate Similarity	NPD1296	Phase 2
0.7386	Intermediate Similarity	NPD3764	Approved
0.7386	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2309	Approved
0.7374	Intermediate Similarity	NPD4287	Approved
0.7368	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7435	Discontinued
0.7365	Intermediate Similarity	NPD1611	Approved
0.7358	Intermediate Similarity	NPD2654	Approved
0.7356	Intermediate Similarity	NPD7472	Approved
0.7355	Intermediate Similarity	NPD447	Suspended
0.7351	Intermediate Similarity	NPD1019	Discontinued
0.7347	Intermediate Similarity	NPD4626	Approved
0.7342	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD3751	Discontinued
0.7337	Intermediate Similarity	NPD6234	Discontinued
0.7333	Intermediate Similarity	NPD1876	Approved
0.733	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6797	Phase 2
0.731	Intermediate Similarity	NPD6808	Phase 2
0.7297	Intermediate Similarity	NPD6776	Approved
0.7297	Intermediate Similarity	NPD6781	Approved
0.7297	Intermediate Similarity	NPD6777	Approved
0.7297	Intermediate Similarity	NPD6782	Approved
0.7297	Intermediate Similarity	NPD6778	Approved
0.7297	Intermediate Similarity	NPD6779	Approved
0.7297	Intermediate Similarity	NPD6780	Approved
0.729	Intermediate Similarity	NPD943	Approved
0.7289	Intermediate Similarity	NPD5889	Approved
0.7289	Intermediate Similarity	NPD5890	Approved
0.7278	Intermediate Similarity	NPD2531	Phase 2
0.7273	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD7251	Discontinued
0.7267	Intermediate Similarity	NPD5242	Approved
0.7263	Intermediate Similarity	NPD8434	Phase 2
0.7263	Intermediate Similarity	NPD8150	Discontinued
0.7248	Intermediate Similarity	NPD1201	Approved
0.7244	Intermediate Similarity	NPD230	Phase 1
0.7235	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD7808	Phase 3
0.7229	Intermediate Similarity	NPD6585	Discontinued
0.7215	Intermediate Similarity	NPD7033	Discontinued
0.7209	Intermediate Similarity	NPD3787	Discontinued
0.7204	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7783	Phase 2
0.7186	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7697	Approved
0.7181	Intermediate Similarity	NPD7698	Approved
0.7181	Intermediate Similarity	NPD7696	Phase 3
0.7178	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6971	Discontinued
0.717	Intermediate Similarity	NPD4476	Approved
0.717	Intermediate Similarity	NPD4477	Approved
0.7153	Intermediate Similarity	NPD5535	Approved
0.7143	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD4908	Phase 1
0.7143	Intermediate Similarity	NPD7871	Phase 2
0.7143	Intermediate Similarity	NPD6279	Approved
0.7143	Intermediate Similarity	NPD6280	Approved
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7874	Approved
0.7134	Intermediate Similarity	NPD5123	Clinical (unspecified phase)

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