NPASS Compound

Structure

NPC470377 OpenBabel07101719132D 46 49 0 0 1 0 0 0 0 0999 V2000 4.6543 4.1638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9028 5.7244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6533 -3.8807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3137 -4.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3219 2.5708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6283 2.9335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9757 1.4311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0864 -2.0276 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6497 -1.2014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4643 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4671 1.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8524 3.2961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9271 4.2933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9514 2.8622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7029 1.3017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6282 0.3044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0326 -3.2696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1610 1.2854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3854 -2.3339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2094 0.9778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6054 -1.6369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6054 -0.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8281 4.7271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6665 -4.0430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3704 2.2632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8767 1.8650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9378 -1.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2729 -1.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2729 -0.4806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9378 -0.4806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7272 -0.1294 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6027 -1.2514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2702 -1.6369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6027 -0.4806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0747 -0.9972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6525 -1.1266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9010 0.4339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7515 -1.5605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1389 -1.7514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1389 0.0194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2702 -2.6369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2225 -2.7070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9757 -1.4311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2702 -0.0952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 7 26 1 0 0 0 0 8 37 1 0 0 0 0 9 37 1 0 0 0 0 10 38 1 0 0 0 0 11 38 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 13 23 2 0 0 0 0 14 26 1 0 0 0 0 15 16 1 0 0 0 0 15 26 2 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 18 20 1 0 0 0 0 18 25 2 0 0 0 0 21 27 1 0 0 0 0 21 28 2 0 0 0 0 22 29 2 0 0 0 0 22 30 1 0 0 0 0 27 30 2 0 0 0 0 27 33 1 0 0 0 0 28 29 1 0 0 0 0 28 41 1 0 0 0 0 29 42 1 0 0 0 0 30 46 1 0 0 0 0 31 16 1 1 0 0 0 31 37 1 0 0 0 0 31 38 1 0 0 0 0 32 33 1 0 0 0 0 32 34 1 0 0 0 0 32 35 2 0 0 0 0 33 43 2 0 0 0 0 34 39 1 0 0 0 0 34 44 2 0 0 0 0 35 40 1 0 0 0 0 35 46 1 0 0 0 0 36 39 1 0 0 0 0 36 40 1 0 0 0 0 36 45 2 0 0 0 0 37 39 1 0 0 0 0 38 40 1 0 0 0 0 39 19 1 6 0 0 0 40 20 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	628.38
Volume:	689.91
LogP:	8.732
LogD:	5.552
LogS:	-4.239
# Rotatable Bonds:	9
TPSA:	104.81
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.163
Synthetic Accessibility Score:	5.64
Fsp3:	0.525
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.025
MDCK Permeability:	1.3462555216392502e-05
Pgp-inhibitor:	0.198
Pgp-substrate:	0.058
Human Intestinal Absorption (HIA):	0.195
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	95.52291107177734%
Volume Distribution (VD):	1.402
Pgp-substrate:	9.31505298614502%

ADMET: Metabolism

CYP1A2-inhibitor:	0.074
CYP1A2-substrate:	0.194
CYP2C19-inhibitor:	0.777
CYP2C19-substrate:	0.337
CYP2C9-inhibitor:	0.926
CYP2C9-substrate:	0.984
CYP2D6-inhibitor:	0.768
CYP2D6-substrate:	0.127
CYP3A4-inhibitor:	0.555
CYP3A4-substrate:	0.524

ADMET: Excretion

Clearance (CL):	5.936
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.255
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.642
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.049
Carcinogencity:	0.09
Eye Corrosion:	0.003
Eye Irritation:	0.864
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC470377

Natural Product ID:	NPC470377
*Common Name:**	Oblongifolin F
IUPAC Name:	n.a.
Synonyms:	Oblongifolin F
Standard InCHIKey:	WWPQYNXDJNETLD-IGFUPLTNSA-N
Standard InCHI:	InChI=1S/C40H52O6/c1-23(2)13-12-14-26(7)15-16-31-37(8,9)39(19-17-24(3)4)34(44)32-33(43)27-21-28(41)29(42)22-30(27)46-35(32)40(36(39)45,38(31,10)11)20-18-25(5)6/h13,15,17-18,21-22,31,41-42H,12,14,16,19-20H2,1-11H3/b26-15+/t31-,39-,40+/m0/s1
SMILES:	C/C(=CC[C@H]1C(C)(C)[C@@]2(CC=C(C)C)C(=O)c3c([C@@](C1(C)C)(C2=O)CC=C(C)C)oc1c(c3=O)cc(c(c1)O)O)/CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2021469
PubChem CID:	70691854
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

*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
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724839]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19113969]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	leaves	Bobai, Guangxi Province, China	2005-Dec	PMID[24679044]
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	Barks	n.a.	n.a.	PMID[24754786]
NPO11471	Garcinia oblongifolia	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	7
Others	3

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	50.0	%	PMID[549757]
NPT165	Cell Line	HeLa	Homo sapiens	FC	>	30.0	n.a.	PMID[549757]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	4200.0	nM	PMID[549757]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	IC50	=	16500.0	nM	PMID[549757]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	7700.0	nM	PMID[549757]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	3000.0	nM	PMID[549757]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	5100.0	nM	PMID[549757]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	2900.0	nM	PMID[549757]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Ratio	=	3.0	n.a.	PMID[549757]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4900.0	nM	PMID[549757]

☑ 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 NPC470377 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	472
0.1-0.2	1814
0.2-0.3	3652
0.3-0.4	9124
0.4-0.5	9410
0.5-0.6	4165
0.6-0.7	5457
0.7-0.8	5776
0.8-0.85	2066
0.85-0.9	685
0.9-0.95	69
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470374
1.0	High Similarity	NPC471975
1.0	High Similarity	NPC478060
1.0	High Similarity	NPC478059
0.9752	High Similarity	NPC471969
0.9313	High Similarity	NPC278427
0.9187	High Similarity	NPC197856
0.9136	High Similarity	NPC470694
0.9108	High Similarity	NPC48949
0.9074	High Similarity	NPC472275
0.9068	High Similarity	NPC172770
0.9068	High Similarity	NPC185258
0.9068	High Similarity	NPC46736
0.9057	High Similarity	NPC476631
0.903	High Similarity	NPC126204
0.9024	High Similarity	NPC156432
0.9018	High Similarity	NPC329760
0.9012	High Similarity	NPC119224
0.9012	High Similarity	NPC297212
0.9012	High Similarity	NPC45146
0.9012	High Similarity	NPC235018
0.9012	High Similarity	NPC476280
0.9006	High Similarity	NPC236796
0.9006	High Similarity	NPC79053
0.8994	High Similarity	NPC249570
0.8963	High Similarity	NPC303460
0.8963	High Similarity	NPC207690
0.8963	High Similarity	NPC306321
0.8957	High Similarity	NPC258331
0.8957	High Similarity	NPC32694
0.8944	High Similarity	NPC142339
0.8938	High Similarity	NPC477047
0.8938	High Similarity	NPC477048
0.8938	High Similarity	NPC89474
0.8902	High Similarity	NPC206605
0.8896	High Similarity	NPC80375
0.8896	High Similarity	NPC320359
0.8889	High Similarity	NPC476630
0.8889	High Similarity	NPC218871
0.8882	High Similarity	NPC113906
0.8882	High Similarity	NPC23553
0.8882	High Similarity	NPC77179
0.8862	High Similarity	NPC476637
0.8855	High Similarity	NPC37870
0.8855	High Similarity	NPC469394
0.8855	High Similarity	NPC39091
0.8848	High Similarity	NPC476295
0.8848	High Similarity	NPC472278
0.8848	High Similarity	NPC270837
0.8848	High Similarity	NPC236132
0.8848	High Similarity	NPC220313
0.8848	High Similarity	NPC473313
0.8848	High Similarity	NPC12461
0.8848	High Similarity	NPC329669
0.8848	High Similarity	NPC189473
0.8848	High Similarity	NPC23298
0.8841	High Similarity	NPC234644
0.8841	High Similarity	NPC167678
0.8841	High Similarity	NPC259456
0.8841	High Similarity	NPC278052
0.8841	High Similarity	NPC29876
0.8841	High Similarity	NPC40491
0.8837	High Similarity	NPC246153
0.8834	High Similarity	NPC100123
0.8834	High Similarity	NPC469658
0.883	High Similarity	NPC476273
0.8827	High Similarity	NPC470762
0.8827	High Similarity	NPC475799
0.8827	High Similarity	NPC138243
0.8827	High Similarity	NPC474167
0.8827	High Similarity	NPC274730
0.8827	High Similarity	NPC3980
0.8827	High Similarity	NPC13779
0.8827	High Similarity	NPC276444
0.8824	High Similarity	NPC478050
0.8812	High Similarity	NPC202157
0.881	High Similarity	NPC101107
0.8795	High Similarity	NPC473286
0.8795	High Similarity	NPC239752
0.8795	High Similarity	NPC275780
0.8795	High Similarity	NPC472450
0.8788	High Similarity	NPC472448
0.8788	High Similarity	NPC83922
0.8788	High Similarity	NPC294965
0.8788	High Similarity	NPC25152
0.878	High Similarity	NPC204290
0.878	High Similarity	NPC228785
0.878	High Similarity	NPC28241
0.878	High Similarity	NPC200746
0.878	High Similarity	NPC476980
0.878	High Similarity	NPC188433
0.878	High Similarity	NPC14353
0.878	High Similarity	NPC139036
0.878	High Similarity	NPC56085
0.8773	High Similarity	NPC469584
0.8773	High Similarity	NPC161960
0.8773	High Similarity	NPC300727
0.8773	High Similarity	NPC241904
0.8773	High Similarity	NPC36852
0.8773	High Similarity	NPC304008
0.8773	High Similarity	NPC262286
0.8773	High Similarity	NPC187745
0.8773	High Similarity	NPC273843
0.8772	High Similarity	NPC221820
0.8765	High Similarity	NPC20830
0.8765	High Similarity	NPC208197
0.8765	High Similarity	NPC256612
0.8765	High Similarity	NPC472048
0.8765	High Similarity	NPC245975
0.875	High Similarity	NPC184136
0.875	High Similarity	NPC475805
0.875	High Similarity	NPC3825
0.875	High Similarity	NPC88804
0.8743	High Similarity	NPC472449
0.8742	High Similarity	NPC118726
0.8742	High Similarity	NPC12367
0.8742	High Similarity	NPC194856
0.8735	High Similarity	NPC7483
0.8735	High Similarity	NPC248638
0.8735	High Similarity	NPC152659
0.8735	High Similarity	NPC236521
0.8728	High Similarity	NPC228209
0.8728	High Similarity	NPC240508
0.8727	High Similarity	NPC66288
0.8727	High Similarity	NPC475883
0.8727	High Similarity	NPC474351
0.8727	High Similarity	NPC57715
0.8727	High Similarity	NPC61010
0.8727	High Similarity	NPC472906
0.872	High Similarity	NPC476242
0.872	High Similarity	NPC329091
0.872	High Similarity	NPC474290
0.872	High Similarity	NPC235448
0.8712	High Similarity	NPC68093
0.8712	High Similarity	NPC317383
0.8712	High Similarity	NPC115853
0.8712	High Similarity	NPC191146
0.8706	High Similarity	NPC469393
0.8704	High Similarity	NPC231018
0.8704	High Similarity	NPC69394
0.8704	High Similarity	NPC170492
0.8704	High Similarity	NPC183878
0.8704	High Similarity	NPC276409
0.8704	High Similarity	NPC280937
0.8704	High Similarity	NPC145379
0.8704	High Similarity	NPC176775
0.8704	High Similarity	NPC47781
0.8704	High Similarity	NPC75279
0.8704	High Similarity	NPC22519
0.8704	High Similarity	NPC250822
0.8704	High Similarity	NPC160951
0.8704	High Similarity	NPC255350
0.8704	High Similarity	NPC274327
0.8698	High Similarity	NPC472276
0.8698	High Similarity	NPC124470
0.8698	High Similarity	NPC109827
0.8696	High Similarity	NPC304295
0.8696	High Similarity	NPC154345
0.8696	High Similarity	NPC205046
0.8696	High Similarity	NPC59162
0.869	High Similarity	NPC476306
0.8686	High Similarity	NPC240808
0.8679	High Similarity	NPC207729
0.8679	High Similarity	NPC239312
0.8679	High Similarity	NPC275772
0.8679	High Similarity	NPC130230
0.8675	High Similarity	NPC78332
0.8675	High Similarity	NPC81679
0.8675	High Similarity	NPC474150
0.8675	High Similarity	NPC229632
0.8675	High Similarity	NPC474162
0.8675	High Similarity	NPC261470
0.8667	High Similarity	NPC475886
0.8667	High Similarity	NPC246478
0.8667	High Similarity	NPC474287
0.8667	High Similarity	NPC476283
0.8667	High Similarity	NPC471973
0.8663	High Similarity	NPC207467
0.8659	High Similarity	NPC218313
0.8659	High Similarity	NPC179732
0.8659	High Similarity	NPC180011
0.8659	High Similarity	NPC472914
0.8659	High Similarity	NPC222814
0.8659	High Similarity	NPC476981
0.8659	High Similarity	NPC474681
0.8659	High Similarity	NPC472911
0.8659	High Similarity	NPC472913
0.8659	High Similarity	NPC129684
0.8659	High Similarity	NPC472910
0.8659	High Similarity	NPC245758
0.8659	High Similarity	NPC165977
0.8659	High Similarity	NPC78225
0.8659	High Similarity	NPC217677
0.8659	High Similarity	NPC237418
0.8659	High Similarity	NPC181960
0.8659	High Similarity	NPC219867
0.8659	High Similarity	NPC96167
0.8659	High Similarity	NPC299520
0.8655	High Similarity	NPC289244
0.8655	High Similarity	NPC227906

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 NPC470377 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	415
0.1-0.2	985
0.2-0.3	1825
0.3-0.4	2691
0.4-0.5	1882
0.5-0.6	869
0.6-0.7	335
0.7-0.8	124
0.8-0.85	22
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8704	High Similarity	NPD2801	Approved
0.8491	Intermediate Similarity	NPD1511	Approved
0.8476	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD1512	Approved
0.8303	Intermediate Similarity	NPD1934	Approved
0.8225	Intermediate Similarity	NPD5494	Approved
0.8204	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD3882	Suspended
0.8125	Intermediate Similarity	NPD2800	Approved
0.8098	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8092	Intermediate Similarity	NPD7473	Discontinued
0.8047	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD3818	Discontinued
0.8036	Intermediate Similarity	NPD7819	Suspended
0.8035	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD6166	Phase 2
0.8	Intermediate Similarity	NPD7054	Approved
0.7988	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD4380	Phase 2
0.7955	Intermediate Similarity	NPD7472	Approved
0.7955	Intermediate Similarity	NPD7074	Phase 3
0.7937	Intermediate Similarity	NPD6099	Approved
0.7937	Intermediate Similarity	NPD6100	Approved
0.7929	Intermediate Similarity	NPD1465	Phase 2
0.7921	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7919	Intermediate Similarity	NPD6232	Discontinued
0.7898	Intermediate Similarity	NPD5844	Phase 1
0.7882	Intermediate Similarity	NPD3817	Phase 2
0.7865	Intermediate Similarity	NPD7251	Discontinued
0.7861	Intermediate Similarity	NPD6959	Discontinued
0.7853	Intermediate Similarity	NPD3750	Approved
0.7853	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD7808	Phase 3
0.7811	Intermediate Similarity	NPD7411	Suspended
0.7809	Intermediate Similarity	NPD6797	Phase 2
0.7791	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD7075	Discontinued
0.7764	Intermediate Similarity	NPD1510	Phase 2
0.776	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD1247	Approved
0.7751	Intermediate Similarity	NPD6599	Discontinued
0.775	Intermediate Similarity	NPD6651	Approved
0.7736	Intermediate Similarity	NPD943	Approved
0.773	Intermediate Similarity	NPD1549	Phase 2
0.7727	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD2796	Approved
0.7709	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3226	Approved
0.7674	Intermediate Similarity	NPD5402	Approved
0.7669	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD2533	Approved
0.7665	Intermediate Similarity	NPD2534	Approved
0.7665	Intermediate Similarity	NPD2532	Approved
0.765	Intermediate Similarity	NPD8434	Phase 2
0.764	Intermediate Similarity	NPD1607	Approved
0.763	Intermediate Similarity	NPD7768	Phase 2
0.7625	Intermediate Similarity	NPD1240	Approved
0.7586	Intermediate Similarity	NPD3749	Approved
0.7558	Intermediate Similarity	NPD6801	Discontinued
0.7546	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3748	Approved
0.7546	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6799	Approved
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7487	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD3926	Phase 2
0.7469	Intermediate Similarity	NPD230	Phase 1
0.7425	Intermediate Similarity	NPD8166	Discontinued
0.7396	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7390	Discontinued
0.7377	Intermediate Similarity	NPD6559	Discontinued
0.7365	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2344	Approved
0.7349	Intermediate Similarity	NPD2346	Discontinued
0.7345	Intermediate Similarity	NPD6234	Discontinued
0.7333	Intermediate Similarity	NPD2799	Discontinued
0.7321	Intermediate Similarity	NPD4628	Phase 3
0.7312	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD8312	Approved
0.7297	Intermediate Similarity	NPD8313	Approved
0.7273	Intermediate Similarity	NPD8150	Discontinued
0.7267	Intermediate Similarity	NPD5403	Approved
0.7267	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD1243	Approved
0.7256	Intermediate Similarity	NPD447	Suspended
0.7253	Intermediate Similarity	NPD7228	Approved
0.7253	Intermediate Similarity	NPD3751	Discontinued
0.7251	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD919	Approved
0.7186	Intermediate Similarity	NPD1551	Phase 2
0.7178	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD3268	Approved
0.7178	Intermediate Similarity	NPD2313	Discontinued
0.7176	Intermediate Similarity	NPD2309	Approved
0.7168	Intermediate Similarity	NPD920	Approved
0.7167	Intermediate Similarity	NPD8127	Discontinued
0.7159	Intermediate Similarity	NPD37	Approved
0.7151	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD5401	Approved
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7135	Intermediate Similarity	NPD4966	Approved
0.7135	Intermediate Similarity	NPD4967	Phase 2
0.7135	Intermediate Similarity	NPD4965	Approved
0.7127	Intermediate Similarity	NPD5710	Approved
0.7127	Intermediate Similarity	NPD5711	Approved
0.712	Intermediate Similarity	NPD7286	Phase 2
0.7119	Intermediate Similarity	NPD5761	Phase 2
0.7119	Intermediate Similarity	NPD5760	Phase 2
0.7118	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD8151	Discontinued
0.7097	Intermediate Similarity	NPD7685	Pre-registration
0.7091	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD1613	Approved
0.7086	Intermediate Similarity	NPD7458	Discontinued
0.7073	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7199	Phase 2
0.7069	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4749	Approved
0.7056	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7907	Approved
0.7052	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5953	Discontinued
0.7041	Intermediate Similarity	NPD6777	Approved
0.7041	Intermediate Similarity	NPD6779	Approved
0.7041	Intermediate Similarity	NPD6780	Approved
0.7041	Intermediate Similarity	NPD6778	Approved
0.7041	Intermediate Similarity	NPD6781	Approved
0.7041	Intermediate Similarity	NPD6776	Approved
0.7041	Intermediate Similarity	NPD6782	Approved
0.7037	Intermediate Similarity	NPD2798	Approved
0.7035	Intermediate Similarity	NPD3300	Phase 2
0.7033	Intermediate Similarity	NPD3787	Discontinued
0.7029	Intermediate Similarity	NPD1653	Approved
0.702	Intermediate Similarity	NPD7696	Phase 3
0.702	Intermediate Similarity	NPD7698	Approved
0.702	Intermediate Similarity	NPD7697	Approved
0.702	Intermediate Similarity	NPD7435	Discontinued
0.7	Intermediate Similarity	NPD9269	Phase 2
0.6995	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD7870	Phase 2
0.6985	Remote Similarity	NPD7871	Phase 2
0.6983	Remote Similarity	NPD4288	Approved
0.6975	Remote Similarity	NPD1470	Approved
0.6974	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6844	Discontinued
0.6965	Remote Similarity	NPD7701	Phase 2
0.6959	Remote Similarity	NPD4363	Phase 3
0.6959	Remote Similarity	NPD4360	Phase 2
0.6957	Remote Similarity	NPD4111	Phase 1
0.6957	Remote Similarity	NPD4665	Approved
0.6951	Remote Similarity	NPD4908	Phase 1
0.6946	Remote Similarity	NPD7801	Approved
0.6946	Remote Similarity	NPD7783	Phase 2
0.6946	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.694	Remote Similarity	NPD7229	Phase 3
0.6936	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7003	Approved
0.6914	Remote Similarity	NPD6273	Approved
0.6909	Remote Similarity	NPD4625	Phase 3
0.6909	Remote Similarity	NPD3027	Phase 3
0.6897	Remote Similarity	NPD7874	Approved
0.6897	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD3972	Approved
0.6893	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.689	Remote Similarity	NPD9494	Approved
0.6884	Remote Similarity	NPD6823	Phase 2
0.6882	Remote Similarity	NPD5405	Approved
0.6882	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5408	Approved
0.6882	Remote Similarity	NPD5404	Approved
0.6882	Remote Similarity	NPD5406	Approved
0.6879	Remote Similarity	NPD6190	Approved
0.6871	Remote Similarity	NPD2797	Approved
0.6871	Remote Similarity	NPD3266	Approved
0.6871	Remote Similarity	NPD1203	Approved
0.6871	Remote Similarity	NPD3267	Approved
0.6853	Remote Similarity	NPD7700	Phase 2
0.6853	Remote Similarity	NPD7699	Phase 2
0.6852	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD1201	Approved
0.6826	Remote Similarity	NPD8032	Phase 2
0.6825	Remote Similarity	NPD7240	Approved
0.6824	Remote Similarity	NPD4308	Phase 3
0.681	Remote Similarity	NPD6696	Suspended
0.68	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5353	Approved
0.679	Remote Similarity	NPD1608	Approved
0.679	Remote Similarity	NPD9717	Approved
0.6786	Remote Similarity	NPD6535	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