NPASS Compound

Structure

NPC470354 OpenBabel07101719522D 39 42 0 0 1 0 0 0 0 0999 V2000 7.3175 4.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0927 5.3461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0873 4.7483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4245 3.1481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5622 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6444 3.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1417 3.3741 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9033 2.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2723 2.3827 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 7.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3515 4.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2179 3.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5622 -0.3660 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 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 2.5981 1.5000 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 1.7321 2.0000 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 0.5000 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 6.0622 1.5000 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 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.0622 -1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -0.3660 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 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 17 1 0 0 0 0 5 18 1 0 0 0 0 6 29 1 0 0 0 0 7 29 1 0 0 0 0 8 12 1 0 0 0 0 8 16 2 0 0 0 0 9 13 1 0 0 0 0 9 17 2 0 0 0 0 10 11 2 0 0 0 0 10 19 1 0 0 0 0 11 29 1 0 0 0 0 12 30 1 0 0 0 0 13 30 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 18 1 0 0 0 0 15 31 1 0 0 0 0 18 32 2 0 0 0 0 19 20 1 0 0 0 0 19 24 2 0 0 0 0 20 39 1 0 0 0 0 21 22 2 0 0 0 0 21 38 1 0 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 25 1 0 0 0 0 23 26 2 0 0 0 0 23 30 1 0 0 0 0 24 33 1 0 0 0 0 25 34 2 0 0 0 0 26 27 1 0 0 0 0 26 38 1 0 0 0 0 27 31 1 0 0 0 0 27 35 2 0 0 0 0 28 30 1 0 0 0 0 28 31 1 0 0 0 0 28 36 2 0 0 0 0 29 39 1 0 0 0 0 31 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.23
Volume:	551.827
LogP:	6.112
LogD:	3.712
LogS:	-3.783
# Rotatable Bonds:	6
TPSA:	131.11
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.386
Synthetic Accessibility Score:	4.397
Fsp3:	0.419
Lipinski Rule-of-5:	Rejected
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:	-4.749
MDCK Permeability:	1.9168115613865666e-05
Pgp-inhibitor:	0.959
Pgp-substrate:	0.927
Human Intestinal Absorption (HIA):	0.579
20% Bioavailability (F20%):	0.118
30% Bioavailability (F30%):	0.214

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	83.8153305053711%
Volume Distribution (VD):	1.245
Pgp-substrate:	10.81039047241211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.1
CYP1A2-substrate:	0.706
CYP2C19-inhibitor:	0.887
CYP2C19-substrate:	0.741
CYP2C9-inhibitor:	0.929
CYP2C9-substrate:	0.705
CYP2D6-inhibitor:	0.861
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.789
CYP3A4-substrate:	0.849

ADMET: Excretion

Clearance (CL):	2.683
Half-life (T1/2):	0.153

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	0.955
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.309
Rat Oral Acute Toxicity:	0.347
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.155
Carcinogencity:	0.841
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.873

Download Data

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

Natural Product: NPC470354

Natural Product ID:	NPC470354
*Common Name:**	Oliganthin D
IUPAC Name:	5,9-dihydroxy-2,2-dimethyl-7,7-bis(3-methylbut-2-enyl)-9-(2-oxopropyl)pyrano[3,2-b]xanthene-6,8,10-trione
Synonyms:	Oliganthin D
Standard InCHIKey:	VDCUEILRTFTERJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C31H34O8/c1-16(2)8-12-30(13-9-17(3)4)23-25(34)22-21(14-20-19(24(22)33)10-11-29(6,7)39-20)38-26(23)27(35)31(37,28(30)36)15-18(5)32/h8-11,14,33,37H,12-13,15H2,1-7H3
SMILES:	CC(=CCC1(C2=C(C(=O)C(C1=O)(CC(=O)C)O)OC3=CC4=C(C=CC(O4)(C)C)C(=C3C2=O)O)CC=C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2013057
PubChem CID:	57345561
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22365754]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27329938]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33296199]
NPO14126	Garcinia oligantha	Species	Clusiaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	7820.0	nM	PMID[532467]

☑ 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 NPC470354 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	458
0.1-0.2	1790
0.2-0.3	4031
0.3-0.4	10209
0.4-0.5	8510
0.5-0.6	4495
0.6-0.7	5662
0.7-0.8	5148
0.8-0.85	2053
0.85-0.9	325
0.9-0.95	12
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9866	High Similarity	NPC470352
0.9664	High Similarity	NPC470353
0.9338	High Similarity	NPC81474
0.9262	High Similarity	NPC329678
0.9128	High Similarity	NPC473813
0.9128	High Similarity	NPC473812
0.9122	High Similarity	NPC316911
0.9122	High Similarity	NPC316560
0.9108	High Similarity	NPC103816
0.9108	High Similarity	NPC61382
0.9073	High Similarity	NPC14001
0.9073	High Similarity	NPC166757
0.9067	High Similarity	NPC472447
0.9067	High Similarity	NPC472446
0.906	High Similarity	NPC323884
0.906	High Similarity	NPC321629
0.906	High Similarity	NPC321148
0.906	High Similarity	NPC326193
0.9051	High Similarity	NPC475106
0.9026	High Similarity	NPC45934
0.902	High Similarity	NPC188403
0.9013	High Similarity	NPC244407
0.9007	High Similarity	NPC220418
0.8933	High Similarity	NPC293852
0.8933	High Similarity	NPC299080
0.8933	High Similarity	NPC78803
0.8933	High Similarity	NPC204469
0.8933	High Similarity	NPC217083
0.8933	High Similarity	NPC214236
0.8933	High Similarity	NPC325346
0.8933	High Similarity	NPC62840
0.8933	High Similarity	NPC59739
0.8919	High Similarity	NPC268178
0.8919	High Similarity	NPC180501
0.8919	High Similarity	NPC54820
0.8903	High Similarity	NPC142527
0.8889	High Similarity	NPC286074
0.8889	High Similarity	NPC54903
0.8889	High Similarity	NPC296869
0.8889	High Similarity	NPC266572
0.8882	High Similarity	NPC120857
0.8882	High Similarity	NPC5820
0.8882	High Similarity	NPC124729
0.8882	High Similarity	NPC85047
0.8882	High Similarity	NPC178343
0.8882	High Similarity	NPC17274
0.8882	High Similarity	NPC476056
0.8882	High Similarity	NPC306488
0.8874	High Similarity	NPC9117
0.8874	High Similarity	NPC190637
0.8874	High Similarity	NPC11700
0.8874	High Similarity	NPC24821
0.8874	High Similarity	NPC293053
0.8874	High Similarity	NPC219915
0.8874	High Similarity	NPC212932
0.8861	High Similarity	NPC125969
0.8854	High Similarity	NPC192587
0.8831	High Similarity	NPC269420
0.8827	High Similarity	NPC193222
0.8824	High Similarity	NPC97716
0.8824	High Similarity	NPC104406
0.8824	High Similarity	NPC24673
0.8824	High Similarity	NPC237635
0.8824	High Similarity	NPC201731
0.8824	High Similarity	NPC79469
0.8816	High Similarity	NPC326500
0.8816	High Similarity	NPC216538
0.8816	High Similarity	NPC311741
0.8816	High Similarity	NPC234629
0.8816	High Similarity	NPC273538
0.8808	High Similarity	NPC200694
0.8808	High Similarity	NPC473042
0.88	High Similarity	NPC471587
0.8792	High Similarity	NPC470669
0.8792	High Similarity	NPC131130
0.8792	High Similarity	NPC477056
0.8792	High Similarity	NPC477055
0.8792	High Similarity	NPC470668
0.879	High Similarity	NPC275575
0.8773	High Similarity	NPC20734
0.8766	High Similarity	NPC6511
0.875	High Similarity	NPC158874
0.875	High Similarity	NPC38219
0.8742	High Similarity	NPC147688
0.8742	High Similarity	NPC156590
0.8742	High Similarity	NPC118840
0.8742	High Similarity	NPC205006
0.8742	High Similarity	NPC64908
0.8733	High Similarity	NPC301217
0.8733	High Similarity	NPC23257
0.8733	High Similarity	NPC96565
0.8733	High Similarity	NPC220062
0.8733	High Similarity	NPC55018
0.8733	High Similarity	NPC303633
0.8733	High Similarity	NPC216978
0.8727	High Similarity	NPC469393
0.8726	High Similarity	NPC311579
0.8726	High Similarity	NPC236756
0.872	High Similarity	NPC193698
0.8718	High Similarity	NPC305965
0.871	High Similarity	NPC469932
0.871	High Similarity	NPC470461
0.871	High Similarity	NPC10027
0.871	High Similarity	NPC288840
0.871	High Similarity	NPC291746
0.871	High Similarity	NPC65775
0.871	High Similarity	NPC5173
0.8704	High Similarity	NPC314653
0.8704	High Similarity	NPC316262
0.8701	High Similarity	NPC473077
0.8701	High Similarity	NPC296998
0.8701	High Similarity	NPC283234
0.8696	High Similarity	NPC94796
0.8693	High Similarity	NPC470674
0.8693	High Similarity	NPC117716
0.8693	High Similarity	NPC470673
0.8693	High Similarity	NPC278175
0.8693	High Similarity	NPC257236
0.8693	High Similarity	NPC319752
0.8688	High Similarity	NPC313368
0.8684	High Similarity	NPC11561
0.8684	High Similarity	NPC144499
0.8684	High Similarity	NPC226636
0.8679	High Similarity	NPC282390
0.8679	High Similarity	NPC281137
0.8679	High Similarity	NPC201127
0.8679	High Similarity	NPC237418
0.8675	High Similarity	NPC477272
0.8675	High Similarity	NPC475680
0.8675	High Similarity	NPC270883
0.8675	High Similarity	NPC159275
0.8675	High Similarity	NPC241100
0.8675	High Similarity	NPC235239
0.8675	High Similarity	NPC150522
0.8675	High Similarity	NPC172986
0.8675	High Similarity	NPC305355
0.8675	High Similarity	NPC261227
0.8671	High Similarity	NPC471116
0.8671	High Similarity	NPC476169
0.8667	High Similarity	NPC474487
0.8667	High Similarity	NPC470672
0.8667	High Similarity	NPC470671
0.8667	High Similarity	NPC201395
0.8667	High Similarity	NPC474504
0.8658	High Similarity	NPC174999
0.8654	High Similarity	NPC61258
0.8654	High Similarity	NPC471115
0.8654	High Similarity	NPC29777
0.8645	High Similarity	NPC160821
0.8645	High Similarity	NPC189087
0.8645	High Similarity	NPC469933
0.8645	High Similarity	NPC470460
0.8645	High Similarity	NPC161191
0.8645	High Similarity	NPC208303
0.8645	High Similarity	NPC132592
0.8645	High Similarity	NPC211811
0.8645	High Similarity	NPC321623
0.8645	High Similarity	NPC161864
0.8642	High Similarity	NPC469395
0.8636	High Similarity	NPC83357
0.8636	High Similarity	NPC195621
0.8636	High Similarity	NPC470458
0.8636	High Similarity	NPC246948
0.8636	High Similarity	NPC312973
0.8636	High Similarity	NPC473135
0.8636	High Similarity	NPC470676
0.8636	High Similarity	NPC475052
0.8636	High Similarity	NPC142405
0.8636	High Similarity	NPC176229
0.8636	High Similarity	NPC473132
0.8636	High Similarity	NPC20488
0.8636	High Similarity	NPC267375
0.8636	High Similarity	NPC301276
0.8636	High Similarity	NPC88964
0.8636	High Similarity	NPC67805
0.8636	High Similarity	NPC474161
0.8636	High Similarity	NPC476088
0.8636	High Similarity	NPC470647
0.8636	High Similarity	NPC111786
0.8636	High Similarity	NPC214774
0.8636	High Similarity	NPC57470
0.8636	High Similarity	NPC54577
0.8627	High Similarity	NPC166138
0.8627	High Similarity	NPC106985
0.8627	High Similarity	NPC18585
0.8618	High Similarity	NPC110969
0.8618	High Similarity	NPC103362
0.8618	High Similarity	NPC282300
0.8618	High Similarity	NPC14871
0.8618	High Similarity	NPC90582
0.8618	High Similarity	NPC262094
0.8616	High Similarity	NPC56049
0.8616	High Similarity	NPC54830
0.8609	High Similarity	NPC78913
0.8609	High Similarity	NPC49242
0.8609	High Similarity	NPC473076
0.8609	High Similarity	NPC217186
0.8609	High Similarity	NPC53181
0.8609	High Similarity	NPC18260
0.8608	High Similarity	NPC178964

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 NPC470354 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	1019
0.2-0.3	1675
0.3-0.4	2747
0.4-0.5	1931
0.5-0.6	931
0.6-0.7	305
0.7-0.8	123
0.8-0.85	18
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8816	High Similarity	NPD4378	Clinical (unspecified phase)
0.8693	High Similarity	NPD7410	Clinical (unspecified phase)
0.8487	Intermediate Similarity	NPD2800	Approved
0.8447	Intermediate Similarity	NPD7075	Discontinued
0.8333	Intermediate Similarity	NPD6651	Approved
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6801	Discontinued
0.8187	Intermediate Similarity	NPD4380	Phase 2
0.8148	Intermediate Similarity	NPD7819	Suspended
0.8137	Intermediate Similarity	NPD7411	Suspended
0.8117	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8117	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD1510	Phase 2
0.8077	Intermediate Similarity	NPD3750	Approved
0.8075	Intermediate Similarity	NPD6599	Discontinued
0.8065	Intermediate Similarity	NPD1549	Phase 2
0.8052	Intermediate Similarity	NPD2796	Approved
0.805	Intermediate Similarity	NPD1512	Approved
0.8037	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD1607	Approved
0.7964	Intermediate Similarity	NPD6959	Discontinued
0.7961	Intermediate Similarity	NPD1240	Approved
0.7939	Intermediate Similarity	NPD3882	Suspended
0.7935	Intermediate Similarity	NPD6099	Approved
0.7935	Intermediate Similarity	NPD6100	Approved
0.7927	Intermediate Similarity	NPD2801	Approved
0.7925	Intermediate Similarity	NPD6799	Approved
0.7925	Intermediate Similarity	NPD1511	Approved
0.7892	Intermediate Similarity	NPD3749	Approved
0.7892	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD5403	Approved
0.7882	Intermediate Similarity	NPD7473	Discontinued
0.7879	Intermediate Similarity	NPD3817	Phase 2
0.7848	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7768	Phase 2
0.7824	Intermediate Similarity	NPD6166	Phase 2
0.7824	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6232	Discontinued
0.7771	Intermediate Similarity	NPD5402	Approved
0.7764	Intermediate Similarity	NPD2534	Approved
0.7764	Intermediate Similarity	NPD2532	Approved
0.7764	Intermediate Similarity	NPD5401	Approved
0.7764	Intermediate Similarity	NPD2533	Approved
0.7759	Intermediate Similarity	NPD7251	Discontinued
0.7758	Intermediate Similarity	NPD1934	Approved
0.7756	Intermediate Similarity	NPD3748	Approved
0.7714	Intermediate Similarity	NPD7808	Phase 3
0.7701	Intermediate Similarity	NPD6797	Phase 2
0.7683	Intermediate Similarity	NPD3226	Approved
0.7673	Intermediate Similarity	NPD1243	Approved
0.7658	Intermediate Similarity	NPD2344	Approved
0.7643	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5953	Discontinued
0.7586	Intermediate Similarity	NPD7054	Approved
0.7569	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD920	Approved
0.7543	Intermediate Similarity	NPD7074	Phase 3
0.7543	Intermediate Similarity	NPD7472	Approved
0.7532	Intermediate Similarity	NPD2799	Discontinued
0.7529	Intermediate Similarity	NPD3818	Discontinued
0.7485	Intermediate Similarity	NPD5494	Approved
0.7485	Intermediate Similarity	NPD7390	Discontinued
0.7484	Intermediate Similarity	NPD2313	Discontinued
0.7484	Intermediate Similarity	NPD1551	Phase 2
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD2309	Approved
0.7457	Intermediate Similarity	NPD3926	Phase 2
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.7442	Intermediate Similarity	NPD1247	Approved
0.7439	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD1471	Phase 3
0.7427	Intermediate Similarity	NPD919	Approved
0.7423	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD7286	Phase 2
0.7375	Intermediate Similarity	NPD2935	Discontinued
0.736	Intermediate Similarity	NPD6559	Discontinued
0.7342	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5124	Phase 1
0.7329	Intermediate Similarity	NPD2346	Discontinued
0.7301	Intermediate Similarity	NPD4628	Phase 3
0.7288	Intermediate Similarity	NPD5844	Phase 1
0.7261	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD422	Phase 1
0.7232	Intermediate Similarity	NPD3751	Discontinued
0.7216	Intermediate Similarity	NPD2403	Approved
0.7207	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4308	Phase 3
0.72	Intermediate Similarity	NPD5711	Approved
0.72	Intermediate Similarity	NPD5710	Approved
0.7197	Intermediate Similarity	NPD4625	Phase 3
0.7193	Intermediate Similarity	NPD1465	Phase 2
0.719	Intermediate Similarity	NPD9717	Approved
0.7173	Intermediate Similarity	NPD7435	Discontinued
0.717	Intermediate Similarity	NPD943	Approved
0.7161	Intermediate Similarity	NPD1203	Approved
0.716	Intermediate Similarity	NPD7458	Discontinued
0.7152	Intermediate Similarity	NPD3268	Approved
0.7151	Intermediate Similarity	NPD4288	Approved
0.7143	Intermediate Similarity	NPD4749	Approved
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7134	Intermediate Similarity	NPD4908	Phase 1
0.7126	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD2798	Approved
0.7112	Intermediate Similarity	NPD4360	Phase 2
0.7112	Intermediate Similarity	NPD4363	Phase 3
0.7105	Intermediate Similarity	NPD6776	Approved
0.7105	Intermediate Similarity	NPD6782	Approved
0.7105	Intermediate Similarity	NPD6777	Approved
0.7105	Intermediate Similarity	NPD6781	Approved
0.7105	Intermediate Similarity	NPD6779	Approved
0.7105	Intermediate Similarity	NPD6778	Approved
0.7105	Intermediate Similarity	NPD6780	Approved
0.7099	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7033	Discontinued
0.7097	Intermediate Similarity	NPD3225	Approved
0.7093	Intermediate Similarity	NPD5760	Phase 2
0.7093	Intermediate Similarity	NPD5761	Phase 2
0.7091	Intermediate Similarity	NPD7003	Approved
0.7083	Intermediate Similarity	NPD7697	Approved
0.7083	Intermediate Similarity	NPD7696	Phase 3
0.7083	Intermediate Similarity	NPD7698	Approved
0.7078	Intermediate Similarity	NPD3972	Approved
0.7065	Intermediate Similarity	NPD8150	Discontinued
0.7051	Intermediate Similarity	NPD1470	Approved
0.7051	Intermediate Similarity	NPD2797	Approved
0.7047	Intermediate Similarity	NPD7871	Phase 2
0.7047	Intermediate Similarity	NPD7870	Phase 2
0.703	Intermediate Similarity	NPD2654	Approved
0.7024	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD3787	Discontinued
0.6995	Remote Similarity	NPD8313	Approved
0.6995	Remote Similarity	NPD8312	Approved
0.6989	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4287	Approved
0.6984	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD4361	Phase 2
0.6978	Remote Similarity	NPD6104	Discontinued
0.6977	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1548	Phase 1
0.6974	Remote Similarity	NPD7584	Approved
0.6957	Remote Similarity	NPD4307	Phase 2
0.6954	Remote Similarity	NPD2296	Approved
0.6954	Remote Similarity	NPD7874	Approved
0.6954	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD5405	Approved
0.6951	Remote Similarity	NPD5408	Approved
0.6951	Remote Similarity	NPD5404	Approved
0.6951	Remote Similarity	NPD5406	Approved
0.6944	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7701	Phase 2
0.6937	Remote Similarity	NPD1296	Phase 2
0.6937	Remote Similarity	NPD411	Approved
0.6937	Remote Similarity	NPD3764	Approved
0.6919	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD447	Suspended
0.691	Remote Similarity	NPD7229	Phase 3
0.6903	Remote Similarity	NPD1201	Approved
0.6903	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD1610	Phase 2
0.6899	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5049	Phase 3
0.6875	Remote Similarity	NPD7095	Approved
0.6872	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD1729	Discontinued
0.686	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD2354	Approved
0.6842	Remote Similarity	NPD6535	Approved
0.6842	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6534	Approved
0.6835	Remote Similarity	NPD3266	Approved
0.6835	Remote Similarity	NPD3267	Approved
0.6834	Remote Similarity	NPD7801	Approved
0.6832	Remote Similarity	NPD6798	Discontinued
0.6823	Remote Similarity	NPD7699	Phase 2
0.6823	Remote Similarity	NPD7700	Phase 2
0.6821	Remote Similarity	NPD6585	Discontinued
0.6818	Remote Similarity	NPD8151	Discontinued
0.6818	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.681	Remote Similarity	NPD230	Phase 1
0.681	Remote Similarity	NPD6355	Discontinued
0.6805	Remote Similarity	NPD3300	Phase 2
0.6788	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD8320	Phase 1
0.6786	Remote Similarity	NPD8319	Approved
0.6784	Remote Similarity	NPD6273	Approved
0.678	Remote Similarity	NPD7907	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