NPASS Compound

Structure

CID166906 OpenBabel06191715542D 34 37 0 0 1 0 0 0 0 0999 V2000 -0.0044 2.9274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2279 3.4139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6943 4.8776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8457 -2.4761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5374 2.4750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6938 2.9269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5386 3.4144 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2271 1.4627 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2268 0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6899 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8448 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8451 -1.4647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 1.9516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8492 3.4148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3831 2.9265 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8495 4.3902 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3828 1.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5368 0.4874 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9763 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6902 -0.9759 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6909 -0.9768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8460 1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6911 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8457 0.4879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0050 4.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5371 1.4632 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5565 -1.4755 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5567 -1.4771 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0199 1.9639 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0053 5.8534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8398 4.3907 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 2 0 0 0 0 3 17 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 28 1 0 0 0 0 13 21 1 0 0 0 0 13 23 1 0 0 0 0 14 24 1 0 0 0 0 14 29 1 0 0 0 0 15 17 1 0 0 0 0 16 2 1 6 0 0 0 16 19 1 0 0 0 0 17 27 1 0 0 0 0 18 4 1 1 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 29 1 6 0 0 0 20 25 1 0 0 0 0 20 29 1 6 0 0 0 21 28 1 6 0 0 0 22 30 1 1 0 0 0 23 25 1 0 0 0 0 23 31 2 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 25 26 2 0 0 0 0 26 28 1 0 0 0 0 27 33 2 0 0 0 0 27 34 1 0 0 0 0 28 5 1 6 0 0 0 29 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.3
Volume:	506.683
LogP:	3.946
LogD:	2.674
LogS:	-4.202
# Rotatable Bonds:	5
TPSA:	91.67
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.547
Synthetic Accessibility Score:	5.502
Fsp3:	0.759
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:	-4.946
MDCK Permeability:	1.8512319002184086e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.889
Human Intestinal Absorption (HIA):	0.299
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.869
Plasma Protein Binding (PPB):	96.64971160888672%
Volume Distribution (VD):	0.672
Pgp-substrate:	3.6877684593200684%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.422
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.868
CYP2C9-inhibitor:	0.034
CYP2C9-substrate:	0.347
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.136
CYP3A4-substrate:	0.247

ADMET: Excretion

Clearance (CL):	16.44
Half-life (T1/2):	0.331

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.745
Drug-inuced Liver Injury (DILI):	0.137
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.861
Maximum Recommended Daily Dose:	0.049
Skin Sensitization:	0.041
Carcinogencity:	0.148
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.436

Download Data

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

Natural Product: NPC166906

Natural Product ID:	NPC166906
*Common Name:**	Zhankuic Acid B
IUPAC Name:	(6R)-6-[(3R,4S,5S,10S,13R,14R,17R)-3-hydroxy-4,10,13-trimethyl-7,11-dioxo-2,3,4,5,6,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methyl-3-methylideneheptanoic acid
Synonyms:	Zhankuic Acid B
Standard InCHIKey:	TXEJUZMIQVTZHO-JNXQNPAGSA-N
Standard InCHI:	InChI=1S/C29H42O5/c1-15(17(3)27(33)34)7-8-16(2)19-9-10-20-25-23(31)13-21-18(4)22(30)11-12-28(21,5)26(25)24(32)14-29(19,20)6/h16-22,30H,1,7-14H2,2-6H3,(H,33,34)/t16-,17?,18+,19-,20+,21+,22-,28+,29-/m1/s1
SMILES:	CC(C(=C)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC(=O)C1=C2C(=O)C[C@@H]2[C@]1(C)CC[C@H]([C@H]2C)O)C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644790
PubChem CID:	53323940
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:0000260] Monohydroxy 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	fruiting body	n.a.	n.a.	PMID[21028898]
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[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
EC50	2
ED50	4
IC50	2

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

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	=	9600.0	nM	PMID[481560]
NPT1184	Cell Line	Daoy	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[481560]
NPT1171	Cell Line	HEp-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[481560]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[481560]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[481560]
NPT91	Cell Line	KB	Homo sapiens	EC50	=	7300.0	nM	PMID[481561]
NPT34	Cell Line	BV-2	Mus musculus	IC50	=	9600.0	nM	PMID[481561]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	EC50	=	8500.0	nM	PMID[481561]

☑ 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 NPC166906 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	173
0.1-0.2	1178
0.2-0.3	4910
0.3-0.4	12001
0.4-0.5	9943
0.5-0.6	6354
0.6-0.7	5339
0.7-0.8	2350
0.8-0.85	247
0.85-0.9	147
0.9-0.95	48
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC470016
0.9886	High Similarity	NPC317586
0.9775	High Similarity	NPC328162
0.9775	High Similarity	NPC305483
0.9775	High Similarity	NPC96859
0.9457	High Similarity	NPC316964
0.9451	High Similarity	NPC43747
0.9444	High Similarity	NPC173875
0.9444	High Similarity	NPC469995
0.9444	High Similarity	NPC174948
0.9444	High Similarity	NPC318282
0.9425	High Similarity	NPC143767
0.9425	High Similarity	NPC131470
0.9425	High Similarity	NPC242864
0.9341	High Similarity	NPC328371
0.9341	High Similarity	NPC95565
0.9318	High Similarity	NPC86319
0.9318	High Similarity	NPC275740
0.9239	High Similarity	NPC320306
0.9231	High Similarity	NPC255809
0.9231	High Similarity	NPC48330
0.9213	High Similarity	NPC183283
0.9205	High Similarity	NPC471722
0.9195	High Similarity	NPC72133
0.9195	High Similarity	NPC28252
0.9195	High Similarity	NPC55309
0.9149	High Similarity	NPC163372
0.9149	High Similarity	NPC302537
0.914	High Similarity	NPC114274
0.913	High Similarity	NPC173272
0.9111	High Similarity	NPC63748
0.9091	High Similarity	NPC159046
0.9091	High Similarity	NPC233836
0.9091	High Similarity	NPC187376
0.9053	High Similarity	NPC308726
0.9053	High Similarity	NPC119601
0.9043	High Similarity	NPC88198
0.9043	High Similarity	NPC327431
0.9043	High Similarity	NPC157787
0.9032	High Similarity	NPC108078
0.9011	High Similarity	NPC69454
0.9011	High Similarity	NPC25750
0.9011	High Similarity	NPC206810
0.9	High Similarity	NPC469400
0.8989	High Similarity	NPC328539
0.8969	High Similarity	NPC323834
0.8936	High Similarity	NPC471717
0.8936	High Similarity	NPC197386
0.8925	High Similarity	NPC249954
0.8913	High Similarity	NPC184870
0.8901	High Similarity	NPC26888
0.8901	High Similarity	NPC23434
0.8901	High Similarity	NPC168027
0.8901	High Similarity	NPC185936
0.8901	High Similarity	NPC297265
0.8889	High Similarity	NPC31985
0.8889	High Similarity	NPC77168
0.8889	High Similarity	NPC84271
0.8889	High Similarity	NPC102414
0.8889	High Similarity	NPC474704
0.8889	High Similarity	NPC1015
0.8889	High Similarity	NPC214387
0.8889	High Similarity	NPC475921
0.8889	High Similarity	NPC474889
0.8878	High Similarity	NPC472925
0.8876	High Similarity	NPC474684
0.8876	High Similarity	NPC142361
0.8876	High Similarity	NPC475740
0.8854	High Similarity	NPC195290
0.8854	High Similarity	NPC204450
0.8851	High Similarity	NPC470015
0.8851	High Similarity	NPC168188
0.8842	High Similarity	NPC51370
0.8842	High Similarity	NPC287833
0.883	High Similarity	NPC18319
0.8817	High Similarity	NPC241156
0.8817	High Similarity	NPC37646
0.8817	High Similarity	NPC200702
0.8817	High Similarity	NPC259286
0.8804	High Similarity	NPC472930
0.8791	High Similarity	NPC148414
0.8791	High Similarity	NPC20388
0.8791	High Similarity	NPC175628
0.8791	High Similarity	NPC191684
0.8791	High Similarity	NPC111585
0.8791	High Similarity	NPC477147
0.8791	High Similarity	NPC477149
0.8788	High Similarity	NPC295244
0.8778	High Similarity	NPC471724
0.8764	High Similarity	NPC145879
0.8764	High Similarity	NPC475022
0.8764	High Similarity	NPC222613
0.8764	High Similarity	NPC118648
0.8764	High Similarity	NPC474778
0.8764	High Similarity	NPC474732
0.8764	High Similarity	NPC474733
0.8764	High Similarity	NPC155011
0.8764	High Similarity	NPC31564
0.8763	High Similarity	NPC55872
0.8763	High Similarity	NPC33973
0.8763	High Similarity	NPC236390
0.8763	High Similarity	NPC251017
0.8763	High Similarity	NPC70967
0.875	High Similarity	NPC472924
0.875	High Similarity	NPC473246
0.8737	High Similarity	NPC10364
0.8723	High Similarity	NPC472941
0.8723	High Similarity	NPC456
0.8723	High Similarity	NPC40765
0.8723	High Similarity	NPC120708
0.8723	High Similarity	NPC243525
0.8723	High Similarity	NPC3772
0.8723	High Similarity	NPC7124
0.8723	High Similarity	NPC125622
0.871	High Similarity	NPC196485
0.871	High Similarity	NPC469406
0.871	High Similarity	NPC245972
0.8696	High Similarity	NPC189520
0.8696	High Similarity	NPC233116
0.8696	High Similarity	NPC86266
0.8696	High Similarity	NPC212301
0.8696	High Similarity	NPC107690
0.8696	High Similarity	NPC110657
0.8681	High Similarity	NPC54689
0.8681	High Similarity	NPC186688
0.8673	High Similarity	NPC216245
0.8673	High Similarity	NPC135854
0.8673	High Similarity	NPC470251
0.8673	High Similarity	NPC96268
0.8673	High Similarity	NPC2436
0.8673	High Similarity	NPC28656
0.8667	High Similarity	NPC58063
0.866	High Similarity	NPC234892
0.866	High Similarity	NPC136289
0.866	High Similarity	NPC473424
0.866	High Similarity	NPC293753
0.8652	High Similarity	NPC94531
0.8652	High Similarity	NPC470574
0.8652	High Similarity	NPC469948
0.8652	High Similarity	NPC311702
0.8652	High Similarity	NPC197823
0.8652	High Similarity	NPC123319
0.8646	High Similarity	NPC476274
0.8646	High Similarity	NPC205899
0.8636	High Similarity	NPC476082
0.8636	High Similarity	NPC278648
0.8632	High Similarity	NPC106557
0.8632	High Similarity	NPC122294
0.8632	High Similarity	NPC121339
0.8617	High Similarity	NPC473170
0.8617	High Similarity	NPC45324
0.8617	High Similarity	NPC472932
0.8617	High Similarity	NPC222845
0.8617	High Similarity	NPC469599
0.8617	High Similarity	NPC69548
0.8617	High Similarity	NPC184848
0.8617	High Similarity	NPC162001
0.8617	High Similarity	NPC139570
0.8614	High Similarity	NPC197428
0.8602	High Similarity	NPC141497
0.8602	High Similarity	NPC477855
0.8602	High Similarity	NPC475255
0.8602	High Similarity	NPC107674
0.8602	High Similarity	NPC470375
0.8602	High Similarity	NPC470254
0.8602	High Similarity	NPC470376
0.8602	High Similarity	NPC170220
0.8587	High Similarity	NPC471896
0.8587	High Similarity	NPC48010
0.8587	High Similarity	NPC289213
0.8586	High Similarity	NPC51452
0.8571	High Similarity	NPC312900
0.8571	High Similarity	NPC53911
0.8571	High Similarity	NPC159442
0.8557	High Similarity	NPC476240
0.8557	High Similarity	NPC124211
0.8557	High Similarity	NPC473514
0.8557	High Similarity	NPC224720
0.8557	High Similarity	NPC476223
0.8557	High Similarity	NPC81530
0.8556	High Similarity	NPC94755
0.8542	High Similarity	NPC477854
0.8542	High Similarity	NPC235464
0.8542	High Similarity	NPC166745
0.8542	High Similarity	NPC16021
0.8539	High Similarity	NPC214043
0.8539	High Similarity	NPC221758
0.8539	High Similarity	NPC59453
0.8539	High Similarity	NPC85774
0.8529	High Similarity	NPC472928
0.8526	High Similarity	NPC477853
0.8526	High Similarity	NPC42042
0.8526	High Similarity	NPC192428
0.8523	High Similarity	NPC260956
0.8523	High Similarity	NPC321289
0.8523	High Similarity	NPC327969
0.8511	High Similarity	NPC49670
0.8511	High Similarity	NPC111015
0.8495	Intermediate Similarity	NPC4036
0.8495	Intermediate Similarity	NPC272746

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 NPC166906 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1551
0.2-0.3	3931
0.3-0.4	2375
0.4-0.5	644
0.5-0.6	184
0.6-0.7	137
0.7-0.8	138
0.8-0.85	36
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9101	High Similarity	NPD5328	Approved
0.8901	High Similarity	NPD6079	Approved
0.8586	High Similarity	NPD6675	Approved
0.8586	High Similarity	NPD5739	Approved
0.8586	High Similarity	NPD6402	Approved
0.8586	High Similarity	NPD7128	Approved
0.8556	High Similarity	NPD3618	Phase 1
0.8539	High Similarity	NPD4786	Approved
0.8526	High Similarity	NPD5221	Approved
0.8526	High Similarity	NPD4697	Phase 3
0.8526	High Similarity	NPD5220	Clinical (unspecified phase)
0.8526	High Similarity	NPD5222	Approved
0.8495	Intermediate Similarity	NPD7515	Phase 2
0.8438	Intermediate Similarity	NPD5173	Approved
0.8438	Intermediate Similarity	NPD4755	Approved
0.8416	Intermediate Similarity	NPD6899	Approved
0.8416	Intermediate Similarity	NPD7320	Approved
0.8416	Intermediate Similarity	NPD6881	Approved
0.8404	Intermediate Similarity	NPD6399	Phase 3
0.8333	Intermediate Similarity	NPD6373	Approved
0.8333	Intermediate Similarity	NPD6372	Approved
0.8317	Intermediate Similarity	NPD5697	Approved
0.8317	Intermediate Similarity	NPD5701	Approved
0.8315	Intermediate Similarity	NPD3667	Approved
0.8265	Intermediate Similarity	NPD4700	Approved
0.8265	Intermediate Similarity	NPD4696	Approved
0.8265	Intermediate Similarity	NPD5286	Approved
0.8265	Intermediate Similarity	NPD5285	Approved
0.8252	Intermediate Similarity	NPD6883	Approved
0.8252	Intermediate Similarity	NPD7290	Approved
0.8252	Intermediate Similarity	NPD7102	Approved
0.8242	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD6011	Approved
0.8211	Intermediate Similarity	NPD4202	Approved
0.8182	Intermediate Similarity	NPD5223	Approved
0.8173	Intermediate Similarity	NPD6650	Approved
0.8173	Intermediate Similarity	NPD6869	Approved
0.8173	Intermediate Similarity	NPD8130	Phase 1
0.8173	Intermediate Similarity	NPD6649	Approved
0.8173	Intermediate Similarity	NPD6847	Approved
0.8173	Intermediate Similarity	NPD6617	Approved
0.8173	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD6013	Approved
0.8155	Intermediate Similarity	NPD6012	Approved
0.8155	Intermediate Similarity	NPD6014	Approved
0.8152	Intermediate Similarity	NPD5279	Phase 3
0.8132	Intermediate Similarity	NPD3665	Phase 1
0.8132	Intermediate Similarity	NPD3133	Approved
0.8132	Intermediate Similarity	NPD3666	Approved
0.8125	Intermediate Similarity	NPD7748	Approved
0.81	Intermediate Similarity	NPD4633	Approved
0.81	Intermediate Similarity	NPD5225	Approved
0.81	Intermediate Similarity	NPD5224	Approved
0.81	Intermediate Similarity	NPD5226	Approved
0.81	Intermediate Similarity	NPD5211	Phase 2
0.8095	Intermediate Similarity	NPD8297	Approved
0.8095	Intermediate Similarity	NPD6882	Approved
0.8061	Intermediate Similarity	NPD6084	Phase 2
0.8061	Intermediate Similarity	NPD6083	Phase 2
0.8041	Intermediate Similarity	NPD5695	Phase 3
0.802	Intermediate Similarity	NPD5175	Approved
0.802	Intermediate Similarity	NPD5174	Approved
0.802	Intermediate Similarity	NPD4754	Approved
0.7979	Intermediate Similarity	NPD5737	Approved
0.7979	Intermediate Similarity	NPD6672	Approved
0.7957	Intermediate Similarity	NPD6409	Approved
0.7957	Intermediate Similarity	NPD6684	Approved
0.7957	Intermediate Similarity	NPD5330	Approved
0.7957	Intermediate Similarity	NPD7146	Approved
0.7957	Intermediate Similarity	NPD7521	Approved
0.7957	Intermediate Similarity	NPD7334	Approved
0.7941	Intermediate Similarity	NPD5141	Approved
0.7917	Intermediate Similarity	NPD5284	Approved
0.7917	Intermediate Similarity	NPD5281	Approved
0.7895	Intermediate Similarity	NPD4753	Phase 2
0.7879	Intermediate Similarity	NPD7902	Approved
0.787	Intermediate Similarity	NPD6868	Approved
0.7864	Intermediate Similarity	NPD6008	Approved
0.7864	Intermediate Similarity	NPD4768	Approved
0.7864	Intermediate Similarity	NPD4767	Approved
0.785	Intermediate Similarity	NPD4632	Approved
0.78	Intermediate Similarity	NPD7638	Approved
0.7789	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD6903	Approved
0.7742	Intermediate Similarity	NPD3668	Phase 3
0.7732	Intermediate Similarity	NPD6411	Approved
0.7732	Intermediate Similarity	NPD8034	Phase 2
0.7732	Intermediate Similarity	NPD8035	Phase 2
0.7727	Intermediate Similarity	NPD6335	Approved
0.7723	Intermediate Similarity	NPD7640	Approved
0.7723	Intermediate Similarity	NPD7639	Approved
0.7717	Intermediate Similarity	NPD4221	Approved
0.7717	Intermediate Similarity	NPD4223	Phase 3
0.7714	Intermediate Similarity	NPD4730	Approved
0.7714	Intermediate Similarity	NPD4729	Approved
0.7714	Intermediate Similarity	NPD5128	Approved
0.7714	Intermediate Similarity	NPD5168	Approved
0.7706	Intermediate Similarity	NPD6274	Approved
0.7677	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD5329	Approved
0.7658	Intermediate Similarity	NPD7101	Approved
0.7658	Intermediate Similarity	NPD7100	Approved
0.764	Intermediate Similarity	NPD6117	Approved
0.7636	Intermediate Similarity	NPD6317	Approved
0.7636	Intermediate Similarity	NPD6009	Approved
0.7636	Intermediate Similarity	NPD7115	Discovery
0.7624	Intermediate Similarity	NPD5696	Approved
0.7579	Intermediate Similarity	NPD5690	Phase 2
0.7579	Intermediate Similarity	NPD4694	Approved
0.7579	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5280	Approved
0.7576	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7900	Approved
0.757	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD5135	Approved
0.757	Intermediate Similarity	NPD5169	Approved
0.757	Intermediate Similarity	NPD5251	Approved
0.757	Intermediate Similarity	NPD5250	Approved
0.757	Intermediate Similarity	NPD5247	Approved
0.757	Intermediate Similarity	NPD5248	Approved
0.757	Intermediate Similarity	NPD4634	Approved
0.757	Intermediate Similarity	NPD5249	Phase 3
0.7568	Intermediate Similarity	NPD6313	Approved
0.7568	Intermediate Similarity	NPD6314	Approved
0.7556	Intermediate Similarity	NPD6116	Phase 1
0.7553	Intermediate Similarity	NPD4197	Approved
0.7551	Intermediate Similarity	NPD6050	Approved
0.7528	Intermediate Similarity	NPD7339	Approved
0.7528	Intermediate Similarity	NPD6942	Approved
0.7526	Intermediate Similarity	NPD6101	Approved
0.7526	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD6673	Approved
0.7526	Intermediate Similarity	NPD6080	Approved
0.7526	Intermediate Similarity	NPD6904	Approved
0.7526	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6909	Approved
0.7522	Intermediate Similarity	NPD6908	Approved
0.75	Intermediate Similarity	NPD5215	Approved
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD5127	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD3573	Approved
0.75	Intermediate Similarity	NPD5217	Approved
0.75	Intermediate Similarity	NPD5216	Approved
0.75	Intermediate Similarity	NPD5210	Approved
0.7473	Intermediate Similarity	NPD3617	Approved
0.7473	Intermediate Similarity	NPD6697	Approved
0.7473	Intermediate Similarity	NPD6115	Approved
0.7473	Intermediate Similarity	NPD6118	Approved
0.7473	Intermediate Similarity	NPD6114	Approved
0.7449	Intermediate Similarity	NPD5692	Phase 3
0.7447	Intermediate Similarity	NPD4788	Approved
0.7434	Intermediate Similarity	NPD6319	Approved
0.7416	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD4688	Approved
0.7396	Intermediate Similarity	NPD4693	Phase 3
0.7396	Intermediate Similarity	NPD5205	Approved
0.7396	Intermediate Similarity	NPD4138	Approved
0.7396	Intermediate Similarity	NPD4690	Approved
0.7396	Intermediate Similarity	NPD4689	Approved
0.7391	Intermediate Similarity	NPD7604	Phase 2
0.7374	Intermediate Similarity	NPD5694	Approved
0.7368	Intermediate Similarity	NPD5983	Phase 2
0.7368	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7492	Approved
0.7312	Intermediate Similarity	NPD4695	Discontinued
0.7297	Intermediate Similarity	NPD5167	Approved
0.7283	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD6059	Approved
0.7281	Intermediate Similarity	NPD6054	Approved
0.7273	Intermediate Similarity	NPD5207	Approved
0.7265	Intermediate Similarity	NPD6616	Approved
0.7265	Intermediate Similarity	NPD6336	Discontinued
0.7253	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5208	Approved
0.7238	Intermediate Similarity	NPD7632	Discontinued
0.7234	Intermediate Similarity	NPD4692	Approved
0.7234	Intermediate Similarity	NPD4139	Approved
0.7228	Intermediate Similarity	NPD6001	Approved
0.7222	Intermediate Similarity	NPD5733	Approved
0.7216	Intermediate Similarity	NPD6098	Approved
0.7203	Intermediate Similarity	NPD8293	Discontinued
0.7203	Intermediate Similarity	NPD7078	Approved
0.72	Intermediate Similarity	NPD5693	Phase 1
0.7191	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD6370	Approved
0.7143	Intermediate Similarity	NPD7736	Approved
0.7143	Intermediate Similarity	NPD3703	Phase 2
0.713	Intermediate Similarity	NPD6412	Phase 2
0.7129	Intermediate Similarity	NPD5779	Approved
0.7129	Intermediate Similarity	NPD5778	Approved
0.7128	Intermediate Similarity	NPD5368	Approved
0.7128	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD4748	Discontinued
0.7117	Intermediate Similarity	NPD6053	Discontinued
0.71	Intermediate Similarity	NPD4096	Approved
0.7087	Intermediate Similarity	NPD7614	Phase 1
0.7079	Intermediate Similarity	NPD4747	Approved
0.7071	Intermediate Similarity	NPD4518	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