NPASS Compound

Structure

NPC470016 OpenBabel07101719522D 35 38 0 0 1 0 0 0 0 0999 V2000 -4.5546 -0.1896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -2.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 -2.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8199 -1.5565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 -0.7248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 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 3.4641 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8855 -0.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1945 -1.8838 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 -5.1727 -2.0917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4817 -3.0428 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8418 -1.3486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 2 0 0 0 0 3 18 1 0 0 0 0 7 35 1 0 0 0 0 8 9 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 20 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 29 1 0 0 0 0 14 22 1 0 0 0 0 14 25 1 0 0 0 0 15 23 1 0 0 0 0 15 26 1 0 0 0 0 16 18 1 0 0 0 0 17 2 1 6 0 0 0 17 20 1 0 0 0 0 18 28 1 0 0 0 0 19 4 1 6 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 30 1 1 0 0 0 21 27 1 0 0 0 0 21 30 1 1 0 0 0 22 29 1 1 0 0 0 23 27 2 0 0 0 0 23 29 1 0 0 0 0 24 31 1 6 0 0 0 25 27 1 0 0 0 0 25 32 2 0 0 0 0 26 30 1 6 0 0 0 26 33 1 0 0 0 0 28 34 2 0 0 0 0 28 35 1 0 0 0 0 29 5 1 1 0 0 0 30 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.33
Volume:	526.615
LogP:	5.276
LogD:	4.875
LogS:	-5.159
# Rotatable Bonds:	6
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.402
Synthetic Accessibility Score:	5.117
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.894
MDCK Permeability:	2.080271406157408e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.936
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.811
30% Bioavailability (F30%):	0.824

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.051
Plasma Protein Binding (PPB):	90.95416259765625%
Volume Distribution (VD):	0.814
Pgp-substrate:	3.171086311340332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.203
CYP1A2-substrate:	0.828
CYP2C19-inhibitor:	0.524
CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.579
CYP2C9-substrate:	0.07
CYP2D6-inhibitor:	0.064
CYP2D6-substrate:	0.061
CYP3A4-inhibitor:	0.934
CYP3A4-substrate:	0.774

ADMET: Excretion

Clearance (CL):	10.546
Half-life (T1/2):	0.271

ADMET: Toxicity

hERG Blockers:	0.66
Human Hepatotoxicity (H-HT):	0.317
Drug-inuced Liver Injury (DILI):	0.1
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.89
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.784
Carcinogencity:	0.016
Eye Corrosion:	0.016
Eye Irritation:	0.029
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC470016

Natural Product ID:	NPC470016
*Common Name:**	Methyl Antcinate H
IUPAC Name:	methyl (6R)-6-[(3R,4S,5S,10S,12S,13R,14R,17R)-3,12-dihydroxy-4,10,13-trimethyl-7-oxo-1,2,3,4,5,6,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-methyl-3-methylideneheptanoate
Synonyms:	Methyl Antcinate H
Standard InCHIKey:	RYROPCNVGGONIU-LAMKLKFSSA-N
Standard InCHI:	InChI=1S/C30H46O5/c1-16(18(3)28(34)35-7)8-9-17(2)20-10-11-21-27-23(15-26(33)30(20,21)6)29(5)13-12-24(31)19(4)22(29)14-25(27)32/h17-22,24,26,31,33H,1,8-15H2,2-7H3/t17-,18?,19+,20-,21+,22+,24-,26+,29+,30-/m1/s1
SMILES:	COC(=O)C(C(=C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)[C@@H](O)CC1=C2C(=O)C[C@@H]2[C@]1(C)CC[C@H]([C@H]2C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644795
PubChem CID:	53325230
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols and derivatives

*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
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[15095145]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17559265]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[17932820]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21028898]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[21115251]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517145]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31891260]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[8594142]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14403	Taiwanofungus camphoratus	Species	Coriolaceae	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
ED50	4
IC50	6

Activity Type	# Activity
Cell Line	6
Individual Protein	1
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT270	Individual Protein	Nitric oxide synthase, inducible	Mus musculus	IC50	=	2500.0	nM	PMID[510364]
NPT1184	Cell Line	Daoy	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[510364]
NPT1171	Cell Line	HEp-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[510364]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[510364]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[510364]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	2500.0	nM	PMID[510365]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	16000.0	nM	PMID[510365]
NPT2	Others	Unspecified		IC50	=	16000.0	nM	PMID[510364]
NPT2	Others	Unspecified		IC50	=	18100.0	nM	PMID[510364]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18100.0	nM	PMID[510365]

☑ 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 NPC470016 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	175
0.1-0.2	1140
0.2-0.3	4726
0.3-0.4	11351
0.4-0.5	10563
0.5-0.6	6153
0.6-0.7	5609
0.7-0.8	2522
0.8-0.85	275
0.85-0.9	137
0.9-0.95	39
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC317586
0.9886	High Similarity	NPC166906
0.9667	High Similarity	NPC96859
0.9667	High Similarity	NPC305483
0.9667	High Similarity	NPC328162
0.9451	High Similarity	NPC328371
0.9355	High Similarity	NPC316964
0.9348	High Similarity	NPC43747
0.9341	High Similarity	NPC318282
0.9341	High Similarity	NPC469995
0.9341	High Similarity	NPC173875
0.9341	High Similarity	NPC174948
0.9318	High Similarity	NPC143767
0.9318	High Similarity	NPC242864
0.9318	High Similarity	NPC131470
0.9239	High Similarity	NPC95565
0.9213	High Similarity	NPC275740
0.9213	High Similarity	NPC86319
0.9158	High Similarity	NPC308726
0.9158	High Similarity	NPC119601
0.9149	High Similarity	NPC88198
0.914	High Similarity	NPC320306
0.913	High Similarity	NPC255809
0.913	High Similarity	NPC48330
0.9111	High Similarity	NPC183283
0.9101	High Similarity	NPC471722
0.9091	High Similarity	NPC72133
0.9091	High Similarity	NPC28252
0.9091	High Similarity	NPC55309
0.9053	High Similarity	NPC302537
0.9053	High Similarity	NPC163372
0.9043	High Similarity	NPC114274
0.9032	High Similarity	NPC173272
0.9022	High Similarity	NPC184870
0.9011	High Similarity	NPC26888
0.9011	High Similarity	NPC63748
0.9011	High Similarity	NPC297265
0.9	High Similarity	NPC474889
0.8989	High Similarity	NPC159046
0.8989	High Similarity	NPC233836
0.8989	High Similarity	NPC187376
0.8947	High Similarity	NPC157787
0.8947	High Similarity	NPC327431
0.8936	High Similarity	NPC108078
0.8936	High Similarity	NPC18319
0.8913	High Similarity	NPC25750
0.8913	High Similarity	NPC206810
0.8913	High Similarity	NPC69454
0.8901	High Similarity	NPC175628
0.8901	High Similarity	NPC20388
0.8901	High Similarity	NPC477149
0.8901	High Similarity	NPC469400
0.8901	High Similarity	NPC111585
0.8901	High Similarity	NPC148414
0.8901	High Similarity	NPC477147
0.8889	High Similarity	NPC328539
0.8878	High Similarity	NPC323834
0.8866	High Similarity	NPC33973
0.8866	High Similarity	NPC70967
0.8866	High Similarity	NPC236390
0.8842	High Similarity	NPC471717
0.8842	High Similarity	NPC197386
0.883	High Similarity	NPC125622
0.883	High Similarity	NPC120708
0.883	High Similarity	NPC7124
0.883	High Similarity	NPC249954
0.883	High Similarity	NPC3772
0.8804	High Similarity	NPC23434
0.8804	High Similarity	NPC185936
0.8804	High Similarity	NPC168027
0.8791	High Similarity	NPC214387
0.8791	High Similarity	NPC77168
0.8791	High Similarity	NPC31985
0.8791	High Similarity	NPC1015
0.8791	High Similarity	NPC474704
0.8791	High Similarity	NPC475921
0.8791	High Similarity	NPC84271
0.8791	High Similarity	NPC102414
0.8788	High Similarity	NPC472925
0.8778	High Similarity	NPC475740
0.8778	High Similarity	NPC474684
0.8778	High Similarity	NPC142361
0.8776	High Similarity	NPC28656
0.8776	High Similarity	NPC470251
0.8776	High Similarity	NPC96268
0.8776	High Similarity	NPC135854
0.8776	High Similarity	NPC2436
0.8776	High Similarity	NPC216245
0.8763	High Similarity	NPC195290
0.8763	High Similarity	NPC136289
0.8763	High Similarity	NPC204450
0.875	High Similarity	NPC168188
0.875	High Similarity	NPC470015
0.875	High Similarity	NPC476274
0.875	High Similarity	NPC51370
0.875	High Similarity	NPC287833
0.875	High Similarity	NPC205899
0.8737	High Similarity	NPC121339
0.8737	High Similarity	NPC106557
0.8723	High Similarity	NPC469599
0.8723	High Similarity	NPC69548
0.8723	High Similarity	NPC241156
0.8723	High Similarity	NPC200702
0.8723	High Similarity	NPC184848
0.8723	High Similarity	NPC259286
0.8723	High Similarity	NPC37646
0.8713	High Similarity	NPC197428
0.871	High Similarity	NPC170220
0.871	High Similarity	NPC472930
0.871	High Similarity	NPC470254
0.871	High Similarity	NPC141497
0.871	High Similarity	NPC107674
0.87	High Similarity	NPC295244
0.8696	High Similarity	NPC191684
0.8696	High Similarity	NPC471896
0.8681	High Similarity	NPC471724
0.8673	High Similarity	NPC159442
0.8673	High Similarity	NPC55872
0.8673	High Similarity	NPC251017
0.8667	High Similarity	NPC31564
0.8667	High Similarity	NPC222613
0.8667	High Similarity	NPC474778
0.8667	High Similarity	NPC145879
0.8667	High Similarity	NPC475022
0.8667	High Similarity	NPC118648
0.8667	High Similarity	NPC474732
0.8667	High Similarity	NPC155011
0.8667	High Similarity	NPC474733
0.866	High Similarity	NPC124211
0.866	High Similarity	NPC476223
0.866	High Similarity	NPC224720
0.866	High Similarity	NPC473514
0.866	High Similarity	NPC81530
0.866	High Similarity	NPC472924
0.866	High Similarity	NPC476240
0.8652	High Similarity	NPC473246
0.8646	High Similarity	NPC10364
0.8646	High Similarity	NPC477854
0.8636	High Similarity	NPC327969
0.8636	High Similarity	NPC321289
0.8632	High Similarity	NPC472941
0.8632	High Similarity	NPC42042
0.8632	High Similarity	NPC456
0.8632	High Similarity	NPC243525
0.8632	High Similarity	NPC40765
0.8617	High Similarity	NPC196485
0.8617	High Similarity	NPC245972
0.8617	High Similarity	NPC469406
0.8602	High Similarity	NPC233116
0.8602	High Similarity	NPC86266
0.8602	High Similarity	NPC189520
0.8602	High Similarity	NPC107690
0.8602	High Similarity	NPC212301
0.8602	High Similarity	NPC110657
0.8587	High Similarity	NPC186688
0.8587	High Similarity	NPC54689
0.8571	High Similarity	NPC56498
0.8571	High Similarity	NPC473788
0.8571	High Similarity	NPC58063
0.8571	High Similarity	NPC53222
0.8571	High Similarity	NPC293753
0.8571	High Similarity	NPC475558
0.8571	High Similarity	NPC234892
0.8571	High Similarity	NPC473424
0.8557	High Similarity	NPC144660
0.8557	High Similarity	NPC299971
0.8557	High Similarity	NPC307954
0.8556	High Similarity	NPC469948
0.8556	High Similarity	NPC94531
0.8556	High Similarity	NPC123319
0.8556	High Similarity	NPC311702
0.8556	High Similarity	NPC197823
0.8556	High Similarity	NPC470574
0.8542	High Similarity	NPC23680
0.8542	High Similarity	NPC253826
0.8542	High Similarity	NPC122294
0.8539	High Similarity	NPC476082
0.8539	High Similarity	NPC278648
0.8526	High Similarity	NPC45324
0.8526	High Similarity	NPC139570
0.8526	High Similarity	NPC222845
0.8526	High Similarity	NPC162001
0.8526	High Similarity	NPC472932
0.8526	High Similarity	NPC473170
0.8511	High Similarity	NPC470375
0.8511	High Similarity	NPC272075
0.8511	High Similarity	NPC470376
0.8511	High Similarity	NPC477435
0.8511	High Similarity	NPC295643
0.8511	High Similarity	NPC475255
0.8511	High Similarity	NPC477436
0.8511	High Similarity	NPC294263
0.8511	High Similarity	NPC477855
0.8511	High Similarity	NPC214756
0.8511	High Similarity	NPC79117
0.8511	High Similarity	NPC470224
0.85	High Similarity	NPC278628
0.85	High Similarity	NPC231530
0.85	High Similarity	NPC51452
0.8495	Intermediate Similarity	NPC289213

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 NPC470016 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1506
0.2-0.3	3907
0.3-0.4	2408
0.4-0.5	681
0.5-0.6	183
0.6-0.7	141
0.7-0.8	133
0.8-0.85	40
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9	High Similarity	NPD5328	Approved
0.8804	High Similarity	NPD6079	Approved
0.8687	High Similarity	NPD6402	Approved
0.8687	High Similarity	NPD6675	Approved
0.8687	High Similarity	NPD5739	Approved
0.8687	High Similarity	NPD7128	Approved
0.8515	High Similarity	NPD6881	Approved
0.8515	High Similarity	NPD6899	Approved
0.8515	High Similarity	NPD7320	Approved
0.8511	High Similarity	NPD6399	Phase 3
0.8462	Intermediate Similarity	NPD3618	Phase 1
0.8444	Intermediate Similarity	NPD4786	Approved
0.8438	Intermediate Similarity	NPD4697	Phase 3
0.8438	Intermediate Similarity	NPD5222	Approved
0.8438	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD5221	Approved
0.8431	Intermediate Similarity	NPD6373	Approved
0.8431	Intermediate Similarity	NPD6372	Approved
0.8416	Intermediate Similarity	NPD5697	Approved
0.8416	Intermediate Similarity	NPD5701	Approved
0.8404	Intermediate Similarity	NPD7515	Phase 2
0.8351	Intermediate Similarity	NPD5173	Approved
0.8351	Intermediate Similarity	NPD4755	Approved
0.835	Intermediate Similarity	NPD7102	Approved
0.835	Intermediate Similarity	NPD6883	Approved
0.835	Intermediate Similarity	NPD7290	Approved
0.8333	Intermediate Similarity	NPD6011	Approved
0.8269	Intermediate Similarity	NPD6847	Approved
0.8269	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8269	Intermediate Similarity	NPD8130	Phase 1
0.8269	Intermediate Similarity	NPD6869	Approved
0.8269	Intermediate Similarity	NPD6649	Approved
0.8269	Intermediate Similarity	NPD6650	Approved
0.8269	Intermediate Similarity	NPD6617	Approved
0.8252	Intermediate Similarity	NPD6012	Approved
0.8252	Intermediate Similarity	NPD6014	Approved
0.8252	Intermediate Similarity	NPD6013	Approved
0.8229	Intermediate Similarity	NPD7748	Approved
0.8222	Intermediate Similarity	NPD3667	Approved
0.819	Intermediate Similarity	NPD6882	Approved
0.819	Intermediate Similarity	NPD8297	Approved
0.8182	Intermediate Similarity	NPD5286	Approved
0.8182	Intermediate Similarity	NPD5285	Approved
0.8182	Intermediate Similarity	NPD4696	Approved
0.8182	Intermediate Similarity	NPD4700	Approved
0.8163	Intermediate Similarity	NPD6084	Phase 2
0.8163	Intermediate Similarity	NPD6083	Phase 2
0.8152	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD5695	Phase 3
0.8125	Intermediate Similarity	NPD4202	Approved
0.81	Intermediate Similarity	NPD5223	Approved
0.8085	Intermediate Similarity	NPD6672	Approved
0.8085	Intermediate Similarity	NPD5737	Approved
0.8065	Intermediate Similarity	NPD7334	Approved
0.8065	Intermediate Similarity	NPD6684	Approved
0.8065	Intermediate Similarity	NPD7521	Approved
0.8065	Intermediate Similarity	NPD6409	Approved
0.8065	Intermediate Similarity	NPD7146	Approved
0.8065	Intermediate Similarity	NPD5330	Approved
0.8065	Intermediate Similarity	NPD5279	Phase 3
0.8043	Intermediate Similarity	NPD3133	Approved
0.8043	Intermediate Similarity	NPD3666	Approved
0.8043	Intermediate Similarity	NPD3665	Phase 1
0.802	Intermediate Similarity	NPD4633	Approved
0.802	Intermediate Similarity	NPD5226	Approved
0.802	Intermediate Similarity	NPD5211	Phase 2
0.802	Intermediate Similarity	NPD5225	Approved
0.802	Intermediate Similarity	NPD5224	Approved
0.798	Intermediate Similarity	NPD7902	Approved
0.7963	Intermediate Similarity	NPD6868	Approved
0.7961	Intermediate Similarity	NPD6008	Approved
0.7944	Intermediate Similarity	NPD4632	Approved
0.7941	Intermediate Similarity	NPD5175	Approved
0.7941	Intermediate Similarity	NPD4754	Approved
0.7941	Intermediate Similarity	NPD5174	Approved
0.79	Intermediate Similarity	NPD7638	Approved
0.7895	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6903	Approved
0.7864	Intermediate Similarity	NPD5141	Approved
0.7835	Intermediate Similarity	NPD5284	Approved
0.7835	Intermediate Similarity	NPD8034	Phase 2
0.7835	Intermediate Similarity	NPD8035	Phase 2
0.7835	Intermediate Similarity	NPD5281	Approved
0.7835	Intermediate Similarity	NPD6411	Approved
0.7822	Intermediate Similarity	NPD7640	Approved
0.7822	Intermediate Similarity	NPD7639	Approved
0.7818	Intermediate Similarity	NPD6335	Approved
0.7812	Intermediate Similarity	NPD4753	Phase 2
0.7798	Intermediate Similarity	NPD6274	Approved
0.7788	Intermediate Similarity	NPD4767	Approved
0.7788	Intermediate Similarity	NPD4768	Approved
0.7778	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD7100	Approved
0.7748	Intermediate Similarity	NPD7101	Approved
0.7727	Intermediate Similarity	NPD7115	Discovery
0.7727	Intermediate Similarity	NPD6009	Approved
0.7727	Intermediate Similarity	NPD6317	Approved
0.7723	Intermediate Similarity	NPD5696	Approved
0.7677	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7900	Approved
0.766	Intermediate Similarity	NPD3668	Phase 3
0.7658	Intermediate Similarity	NPD6314	Approved
0.7658	Intermediate Similarity	NPD6313	Approved
0.7653	Intermediate Similarity	NPD6050	Approved
0.7642	Intermediate Similarity	NPD5128	Approved
0.7642	Intermediate Similarity	NPD4730	Approved
0.7642	Intermediate Similarity	NPD4729	Approved
0.7642	Intermediate Similarity	NPD5168	Approved
0.7634	Intermediate Similarity	NPD4223	Phase 3
0.7634	Intermediate Similarity	NPD4221	Approved
0.7629	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD6904	Approved
0.7629	Intermediate Similarity	NPD6673	Approved
0.7629	Intermediate Similarity	NPD6080	Approved
0.7629	Intermediate Similarity	NPD6101	Approved
0.7611	Intermediate Similarity	NPD6909	Approved
0.7611	Intermediate Similarity	NPD6908	Approved
0.7604	Intermediate Similarity	NPD3573	Approved
0.7579	Intermediate Similarity	NPD5329	Approved
0.7556	Intermediate Similarity	NPD6117	Approved
0.7551	Intermediate Similarity	NPD5692	Phase 3
0.7522	Intermediate Similarity	NPD6319	Approved
0.75	Intermediate Similarity	NPD5248	Approved
0.75	Intermediate Similarity	NPD5247	Approved
0.75	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5250	Approved
0.75	Intermediate Similarity	NPD5690	Phase 2
0.75	Intermediate Similarity	NPD5249	Phase 3
0.75	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5280	Approved
0.75	Intermediate Similarity	NPD4694	Approved
0.75	Intermediate Similarity	NPD5251	Approved
0.75	Intermediate Similarity	NPD4634	Approved
0.75	Intermediate Similarity	NPD5135	Approved
0.75	Intermediate Similarity	NPD5169	Approved
0.7478	Intermediate Similarity	NPD7604	Phase 2
0.7475	Intermediate Similarity	NPD5694	Approved
0.7474	Intermediate Similarity	NPD4197	Approved
0.7473	Intermediate Similarity	NPD6116	Phase 1
0.7456	Intermediate Similarity	NPD5983	Phase 2
0.7456	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7339	Approved
0.7444	Intermediate Similarity	NPD6942	Approved
0.7431	Intermediate Similarity	NPD5127	Approved
0.7431	Intermediate Similarity	NPD5216	Approved
0.7431	Intermediate Similarity	NPD5215	Approved
0.7431	Intermediate Similarity	NPD5217	Approved
0.7426	Intermediate Similarity	NPD5210	Approved
0.7426	Intermediate Similarity	NPD4629	Approved
0.7419	Intermediate Similarity	NPD7525	Registered
0.7414	Intermediate Similarity	NPD7492	Approved
0.7391	Intermediate Similarity	NPD6118	Approved
0.7391	Intermediate Similarity	NPD6115	Approved
0.7391	Intermediate Similarity	NPD3617	Approved
0.7391	Intermediate Similarity	NPD6114	Approved
0.7391	Intermediate Similarity	NPD6697	Approved
0.7374	Intermediate Similarity	NPD5207	Approved
0.7368	Intermediate Similarity	NPD6054	Approved
0.7368	Intermediate Similarity	NPD6059	Approved
0.7368	Intermediate Similarity	NPD4788	Approved
0.735	Intermediate Similarity	NPD6336	Discontinued
0.735	Intermediate Similarity	NPD6616	Approved
0.7347	Intermediate Similarity	NPD5208	Approved
0.7333	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7632	Discontinued
0.7327	Intermediate Similarity	NPD6001	Approved
0.732	Intermediate Similarity	NPD4693	Phase 3
0.732	Intermediate Similarity	NPD6098	Approved
0.732	Intermediate Similarity	NPD4138	Approved
0.732	Intermediate Similarity	NPD4689	Approved
0.732	Intermediate Similarity	NPD4690	Approved
0.732	Intermediate Similarity	NPD5205	Approved
0.732	Intermediate Similarity	NPD4688	Approved
0.73	Intermediate Similarity	NPD5693	Phase 1
0.7288	Intermediate Similarity	NPD7078	Approved
0.7288	Intermediate Similarity	NPD8293	Discontinued
0.7241	Intermediate Similarity	NPD6370	Approved
0.7234	Intermediate Similarity	NPD4695	Discontinued
0.7232	Intermediate Similarity	NPD5167	Approved
0.7228	Intermediate Similarity	NPD5778	Approved
0.7228	Intermediate Similarity	NPD5779	Approved
0.7227	Intermediate Similarity	NPD7736	Approved
0.7222	Intermediate Similarity	NPD6412	Phase 2
0.7207	Intermediate Similarity	NPD6053	Discontinued
0.7204	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4692	Approved
0.7158	Intermediate Similarity	NPD4139	Approved
0.7155	Intermediate Similarity	NPD6015	Approved
0.7155	Intermediate Similarity	NPD6016	Approved
0.7143	Intermediate Similarity	NPD5733	Approved
0.7111	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5988	Approved
0.7087	Intermediate Similarity	NPD5654	Approved
0.7083	Intermediate Similarity	NPD6435	Approved
0.7065	Intermediate Similarity	NPD3703	Phase 2
0.7059	Intermediate Similarity	NPD7507	Approved
0.7053	Intermediate Similarity	NPD8259	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