NPASS Compound

Structure

CID323834 OpenBabel06191716172D 35 38 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 -0.0003 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 0.8457 -2.4761 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 -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 -1.6909 -0.9768 0.0000 C 0 0 1 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 0.0003 -0.9763 0.0000 C 0 0 2 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 -1.6911 -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 0.8454 -1.4643 0.0000 C 0 0 1 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 2.5565 -1.4755 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 1.7114 -1.9643 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 18 1 0 0 0 0 10 19 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 20 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 28 1 0 0 0 0 15 17 1 0 0 0 0 16 2 1 6 0 0 0 16 18 1 0 0 0 0 17 26 1 0 0 0 0 18 28 1 6 0 0 0 19 24 1 0 0 0 0 19 28 1 6 0 0 0 20 24 1 0 0 0 0 20 30 1 6 0 0 0 21 25 1 0 0 0 0 21 31 2 0 0 0 0 22 27 1 6 0 0 0 22 29 1 0 0 0 0 23 29 1 1 0 0 0 23 32 1 0 0 0 0 24 25 2 0 0 0 0 25 27 1 0 0 0 0 26 33 2 0 0 0 0 26 34 1 0 0 0 0 27 4 1 6 0 0 0 28 5 1 6 0 0 0 29 6 1 1 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	488.31
Volume:	518.11
LogP:	3.761
LogD:	2.535
LogS:	-3.828
# Rotatable Bonds:	5
TPSA:	111.9
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.494
Synthetic Accessibility Score:	5.243
Fsp3:	0.828
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:	-5.294
MDCK Permeability:	2.8856060453108512e-05
Pgp-inhibitor:	0.051
Pgp-substrate:	0.026
Human Intestinal Absorption (HIA):	0.102
20% Bioavailability (F20%):	0.87
30% Bioavailability (F30%):	0.611

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.345
Plasma Protein Binding (PPB):	94.12467193603516%
Volume Distribution (VD):	0.544
Pgp-substrate:	3.990230083465576%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.277
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.82
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.62
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.144
CYP3A4-inhibitor:	0.075
CYP3A4-substrate:	0.132

ADMET: Excretion

Clearance (CL):	5.309
Half-life (T1/2):	0.66

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.896
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.874
Maximum Recommended Daily Dose:	0.512
Skin Sensitization:	0.088
Carcinogencity:	0.01
Eye Corrosion:	0.006
Eye Irritation:	0.019
Respiratory Toxicity:	0.581

Download Data

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

Natural Product: NPC323834

Natural Product ID:	NPC323834
*Common Name:**	Antcin K
IUPAC Name:	(6R)-2-methyl-3-methylidene-6-[(3R,4R,5R,7S,10S,13R,14R,17R)-3,4,7-trihydroxy-4,10,13-trimethyl-11-oxo-2,3,5,6,7,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanoic acid
Synonyms:	Antcin K
Standard InCHIKey:	RWTLLOHEXIZDCG-DOZCWRSDSA-N
Standard InCHI:	InChI=1S/C29H44O6/c1-15(17(3)26(33)34)7-8-16(2)18-9-10-19-24-20(30)13-22-27(4,12-11-23(32)29(22,6)35)25(24)21(31)14-28(18,19)5/h16-20,22-23,30,32,35H,1,7-14H2,2-6H3,(H,33,34)/t16-,17?,18-,19+,20+,22-,23-,27+,28-,29-/m1/s1
SMILES:	CC(CCC(=C)C(C)C(=O)O)C1CCC2C1(CC(=O)C3=C2C(CC4C3(CCC(C4(C)O)O)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1644794
PubChem CID:	53321283
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:0001104] Trihydroxy 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	2

Activity Type	# Activity
Cell Line	4
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1184	Cell Line	Daoy	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[538095]
NPT1171	Cell Line	HEp-2	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[538095]
NPT83	Cell Line	MCF7	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[538095]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[538095]
NPT2	Others	Unspecified		IC50	=	47200.0	nM	PMID[538095]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	47200.0	nM	PMID[538096]

☑ 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 NPC323834 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	201
0.1-0.2	1239
0.2-0.3	4137
0.3-0.4	8212
0.4-0.5	12979
0.5-0.6	6539
0.6-0.7	6573
0.7-0.8	2482
0.8-0.85	227
0.85-0.9	94
0.9-0.95	11
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC316964
0.9278	High Similarity	NPC320306
0.9192	High Similarity	NPC163372
0.9192	High Similarity	NPC302537
0.9118	High Similarity	NPC220229
0.9118	High Similarity	NPC475060
0.91	High Similarity	NPC308726
0.91	High Similarity	NPC119601
0.9091	High Similarity	NPC327431
0.9072	High Similarity	NPC318282
0.9072	High Similarity	NPC469995
0.9072	High Similarity	NPC200702
0.9072	High Similarity	NPC174948
0.9072	High Similarity	NPC173875
0.9029	High Similarity	NPC217201
0.902	High Similarity	NPC85829
0.902	High Similarity	NPC49958
0.902	High Similarity	NPC302607
0.902	High Similarity	NPC97202
0.902	High Similarity	NPC214264
0.902	High Similarity	NPC50692
0.902	High Similarity	NPC319077
0.902	High Similarity	NPC476027
0.902	High Similarity	NPC152695
0.902	High Similarity	NPC171137
0.902	High Similarity	NPC150531
0.902	High Similarity	NPC48733
0.902	High Similarity	NPC296945
0.902	High Similarity	NPC202167
0.902	High Similarity	NPC149047
0.902	High Similarity	NPC260268
0.901	High Similarity	NPC55872
0.898	High Similarity	NPC328371
0.8969	High Similarity	NPC166906
0.8962	High Similarity	NPC250109
0.8962	High Similarity	NPC962
0.8942	High Similarity	NPC11710
0.8932	High Similarity	NPC472925
0.8932	High Similarity	NPC83744
0.8922	High Similarity	NPC209502
0.8922	High Similarity	NPC28656
0.8922	High Similarity	NPC204833
0.8911	High Similarity	NPC473424
0.8878	High Similarity	NPC470016
0.8878	High Similarity	NPC317586
0.8846	High Similarity	NPC65941
0.8846	High Similarity	NPC329417
0.8824	High Similarity	NPC251017
0.8812	High Similarity	NPC472924
0.8796	High Similarity	NPC266728
0.8796	High Similarity	NPC49492
0.8788	High Similarity	NPC328162
0.8788	High Similarity	NPC96859
0.8788	High Similarity	NPC7124
0.8788	High Similarity	NPC305483
0.8788	High Similarity	NPC249954
0.8763	High Similarity	NPC233116
0.8763	High Similarity	NPC63748
0.875	High Similarity	NPC477916
0.8727	High Similarity	NPC475041
0.8725	High Similarity	NPC477915
0.8725	High Similarity	NPC204450
0.8725	High Similarity	NPC195290
0.8725	High Similarity	NPC234892
0.8725	High Similarity	NPC293753
0.87	High Similarity	NPC122294
0.87	High Similarity	NPC18319
0.8687	High Similarity	NPC48330
0.8687	High Similarity	NPC259286
0.8679	High Similarity	NPC473036
0.8679	High Similarity	NPC272898
0.8673	High Similarity	NPC69454
0.866	High Similarity	NPC289213
0.866	High Similarity	NPC136801
0.866	High Similarity	NPC469400
0.8654	High Similarity	NPC51452
0.8641	High Similarity	NPC236390
0.8614	High Similarity	NPC471717
0.8614	High Similarity	NPC16021
0.8614	High Similarity	NPC197386
0.8614	High Similarity	NPC10364
0.8614	High Similarity	NPC114274
0.8611	High Similarity	NPC108721
0.8611	High Similarity	NPC73300
0.86	High Similarity	NPC173272
0.8598	High Similarity	NPC472928
0.8598	High Similarity	NPC188738
0.8586	High Similarity	NPC184870
0.8586	High Similarity	NPC470957
0.8586	High Similarity	NPC470958
0.8586	High Similarity	NPC196227
0.8571	High Similarity	NPC473037
0.8558	High Similarity	NPC477812
0.8557	High Similarity	NPC214387
0.8544	High Similarity	NPC136289
0.8529	High Similarity	NPC476274
0.8529	High Similarity	NPC299971
0.8529	High Similarity	NPC205899
0.8529	High Similarity	NPC307954
0.8529	High Similarity	NPC287833
0.8529	High Similarity	NPC51370
0.8529	High Similarity	NPC154072
0.8529	High Similarity	NPC144660
0.8519	High Similarity	NPC207251
0.8515	High Similarity	NPC108078
0.8515	High Similarity	NPC43747
0.8505	High Similarity	NPC76084
0.85	High Similarity	NPC271195
0.85	High Similarity	NPC53565
0.85	High Similarity	NPC37646
0.8496	Intermediate Similarity	NPC269642
0.8496	Intermediate Similarity	NPC222688
0.8491	Intermediate Similarity	NPC295244
0.8491	Intermediate Similarity	NPC472217
0.8491	Intermediate Similarity	NPC472219
0.8491	Intermediate Similarity	NPC472218
0.8485	Intermediate Similarity	NPC472930
0.8485	Intermediate Similarity	NPC206810
0.8482	Intermediate Similarity	NPC109973
0.8476	Intermediate Similarity	NPC166607
0.8469	Intermediate Similarity	NPC477149
0.8469	Intermediate Similarity	NPC477147
0.8455	Intermediate Similarity	NPC176840
0.8455	Intermediate Similarity	NPC190286
0.8454	Intermediate Similarity	NPC242864
0.8454	Intermediate Similarity	NPC143767
0.8454	Intermediate Similarity	NPC131470
0.8447	Intermediate Similarity	NPC81530
0.8447	Intermediate Similarity	NPC476240
0.8447	Intermediate Similarity	NPC476223
0.8447	Intermediate Similarity	NPC224720
0.844	Intermediate Similarity	NPC472926
0.844	Intermediate Similarity	NPC317210
0.8421	Intermediate Similarity	NPC473979
0.8416	Intermediate Similarity	NPC3772
0.8416	Intermediate Similarity	NPC243525
0.8416	Intermediate Similarity	NPC95565
0.8416	Intermediate Similarity	NPC471463
0.8416	Intermediate Similarity	NPC117133
0.8416	Intermediate Similarity	NPC472941
0.8416	Intermediate Similarity	NPC456
0.8416	Intermediate Similarity	NPC40765
0.8411	Intermediate Similarity	NPC214644
0.8411	Intermediate Similarity	NPC286174
0.8411	Intermediate Similarity	NPC77947
0.8407	Intermediate Similarity	NPC46570
0.8407	Intermediate Similarity	NPC202051
0.84	Intermediate Similarity	NPC472977
0.84	Intermediate Similarity	NPC119562
0.84	Intermediate Similarity	NPC279410
0.84	Intermediate Similarity	NPC472976
0.84	Intermediate Similarity	NPC469406
0.8396	Intermediate Similarity	NPC230541
0.8384	Intermediate Similarity	NPC189520
0.8384	Intermediate Similarity	NPC116726
0.8384	Intermediate Similarity	NPC73457
0.8384	Intermediate Similarity	NPC155304
0.8384	Intermediate Similarity	NPC107690
0.8381	Intermediate Similarity	NPC160843
0.8381	Intermediate Similarity	NPC96268
0.8378	Intermediate Similarity	NPC55296
0.8378	Intermediate Similarity	NPC471854
0.8367	Intermediate Similarity	NPC86319
0.8367	Intermediate Similarity	NPC275740
0.8365	Intermediate Similarity	NPC56498
0.8365	Intermediate Similarity	NPC281702
0.8364	Intermediate Similarity	NPC326542
0.8351	Intermediate Similarity	NPC138756
0.835	Intermediate Similarity	NPC198880
0.835	Intermediate Similarity	NPC470074
0.8349	Intermediate Similarity	NPC472002
0.8349	Intermediate Similarity	NPC236217
0.8333	Intermediate Similarity	NPC107493
0.8333	Intermediate Similarity	NPC106557
0.8333	Intermediate Similarity	NPC161147
0.8333	Intermediate Similarity	NPC121339
0.8333	Intermediate Similarity	NPC37116
0.8333	Intermediate Similarity	NPC129689
0.8333	Intermediate Similarity	NPC197428
0.8319	Intermediate Similarity	NPC79579
0.8317	Intermediate Similarity	NPC266899
0.8317	Intermediate Similarity	NPC297199
0.8317	Intermediate Similarity	NPC473170
0.8317	Intermediate Similarity	NPC255809
0.8317	Intermediate Similarity	NPC472932
0.8304	Intermediate Similarity	NPC153440
0.8302	Intermediate Similarity	NPC102352
0.83	Intermediate Similarity	NPC470254
0.83	Intermediate Similarity	NPC243866
0.83	Intermediate Similarity	NPC109305
0.8286	Intermediate Similarity	NPC159442
0.8286	Intermediate Similarity	NPC249187
0.8286	Intermediate Similarity	NPC191892
0.8286	Intermediate Similarity	NPC247957
0.8286	Intermediate Similarity	NPC475050
0.8283	Intermediate Similarity	NPC48010
0.8283	Intermediate Similarity	NPC183283
0.8276	Intermediate Similarity	NPC293112
0.8273	Intermediate Similarity	NPC194100
0.8269	Intermediate Similarity	NPC97435

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 NPC323834 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	169
0.1-0.2	1604
0.2-0.3	3792
0.3-0.4	2340
0.4-0.5	748
0.5-0.6	197
0.6-0.7	189
0.7-0.8	111
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD5328	Approved
0.8131	Intermediate Similarity	NPD7128	Approved
0.8131	Intermediate Similarity	NPD5739	Approved
0.8131	Intermediate Similarity	NPD6675	Approved
0.8131	Intermediate Similarity	NPD6402	Approved
0.8108	Intermediate Similarity	NPD4632	Approved
0.802	Intermediate Similarity	NPD6079	Approved
0.8019	Intermediate Similarity	NPD5211	Phase 2
0.7982	Intermediate Similarity	NPD6881	Approved
0.7982	Intermediate Similarity	NPD6899	Approved
0.7982	Intermediate Similarity	NPD7320	Approved
0.7981	Intermediate Similarity	NPD4755	Approved
0.7909	Intermediate Similarity	NPD6373	Approved
0.7909	Intermediate Similarity	NPD6372	Approved
0.7895	Intermediate Similarity	NPD7115	Discovery
0.789	Intermediate Similarity	NPD5701	Approved
0.789	Intermediate Similarity	NPD5697	Approved
0.787	Intermediate Similarity	NPD5141	Approved
0.7857	Intermediate Similarity	NPD8297	Approved
0.7838	Intermediate Similarity	NPD7290	Approved
0.7838	Intermediate Similarity	NPD7102	Approved
0.7838	Intermediate Similarity	NPD4634	Approved
0.7838	Intermediate Similarity	NPD6883	Approved
0.783	Intermediate Similarity	NPD4696	Approved
0.783	Intermediate Similarity	NPD5285	Approved
0.783	Intermediate Similarity	NPD7639	Approved
0.783	Intermediate Similarity	NPD4700	Approved
0.783	Intermediate Similarity	NPD5286	Approved
0.783	Intermediate Similarity	NPD7640	Approved
0.7818	Intermediate Similarity	NPD6011	Approved
0.7798	Intermediate Similarity	NPD6008	Approved
0.7768	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7768	Intermediate Similarity	NPD6869	Approved
0.7768	Intermediate Similarity	NPD6847	Approved
0.7768	Intermediate Similarity	NPD6649	Approved
0.7768	Intermediate Similarity	NPD8130	Phase 1
0.7768	Intermediate Similarity	NPD6650	Approved
0.7768	Intermediate Similarity	NPD6617	Approved
0.7767	Intermediate Similarity	NPD4202	Approved
0.7767	Intermediate Similarity	NPD6399	Phase 3
0.7757	Intermediate Similarity	NPD5223	Approved
0.7748	Intermediate Similarity	NPD6013	Approved
0.7748	Intermediate Similarity	NPD6014	Approved
0.7748	Intermediate Similarity	NPD6012	Approved
0.7739	Intermediate Similarity	NPD6009	Approved
0.7736	Intermediate Similarity	NPD7638	Approved
0.7714	Intermediate Similarity	NPD5222	Approved
0.7714	Intermediate Similarity	NPD5221	Approved
0.7714	Intermediate Similarity	NPD4697	Phase 3
0.7714	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD3618	Phase 1
0.7699	Intermediate Similarity	NPD6882	Approved
0.7692	Intermediate Similarity	NPD6319	Approved
0.7685	Intermediate Similarity	NPD5224	Approved
0.7685	Intermediate Similarity	NPD5225	Approved
0.7685	Intermediate Similarity	NPD4633	Approved
0.7685	Intermediate Similarity	NPD5226	Approved
0.7677	Intermediate Similarity	NPD4786	Approved
0.767	Intermediate Similarity	NPD7515	Phase 2
0.7642	Intermediate Similarity	NPD5173	Approved
0.7615	Intermediate Similarity	NPD4754	Approved
0.7615	Intermediate Similarity	NPD5174	Approved
0.7615	Intermediate Similarity	NPD5175	Approved
0.7589	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD7507	Approved
0.75	Intermediate Similarity	NPD5281	Approved
0.75	Intermediate Similarity	NPD5284	Approved
0.75	Intermediate Similarity	NPD7604	Phase 2
0.7479	Intermediate Similarity	NPD5983	Phase 2
0.7477	Intermediate Similarity	NPD4768	Approved
0.7477	Intermediate Similarity	NPD6084	Phase 2
0.7477	Intermediate Similarity	NPD4767	Approved
0.7477	Intermediate Similarity	NPD6083	Phase 2
0.7475	Intermediate Similarity	NPD3667	Approved
0.7453	Intermediate Similarity	NPD5695	Phase 3
0.7438	Intermediate Similarity	NPD7492	Approved
0.7426	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD6054	Approved
0.7395	Intermediate Similarity	NPD6059	Approved
0.7391	Intermediate Similarity	NPD6053	Discontinued
0.7377	Intermediate Similarity	NPD6336	Discontinued
0.7377	Intermediate Similarity	NPD6616	Approved
0.7373	Intermediate Similarity	NPD6335	Approved
0.7364	Intermediate Similarity	NPD7632	Discontinued
0.7358	Intermediate Similarity	NPD7748	Approved
0.7353	Intermediate Similarity	NPD5279	Phase 3
0.735	Intermediate Similarity	NPD6274	Approved
0.7345	Intermediate Similarity	NPD4729	Approved
0.7345	Intermediate Similarity	NPD5128	Approved
0.7345	Intermediate Similarity	NPD4730	Approved
0.7339	Intermediate Similarity	NPD7319	Approved
0.7327	Intermediate Similarity	NPD3665	Phase 1
0.7327	Intermediate Similarity	NPD3666	Approved
0.7327	Intermediate Similarity	NPD3133	Approved
0.7317	Intermediate Similarity	NPD7078	Approved
0.7317	Intermediate Similarity	NPD8293	Discontinued
0.7315	Intermediate Similarity	NPD7902	Approved
0.7311	Intermediate Similarity	NPD7100	Approved
0.7311	Intermediate Similarity	NPD7101	Approved
0.7308	Intermediate Similarity	NPD4753	Phase 2
0.7288	Intermediate Similarity	NPD6317	Approved
0.7273	Intermediate Similarity	NPD6370	Approved
0.7264	Intermediate Similarity	NPD5778	Approved
0.7264	Intermediate Similarity	NPD5779	Approved
0.7258	Intermediate Similarity	NPD7736	Approved
0.7257	Intermediate Similarity	NPD6412	Phase 2
0.7227	Intermediate Similarity	NPD6313	Approved
0.7227	Intermediate Similarity	NPD6314	Approved
0.7217	Intermediate Similarity	NPD5249	Phase 3
0.7217	Intermediate Similarity	NPD5135	Approved
0.7217	Intermediate Similarity	NPD5248	Approved
0.7217	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5247	Approved
0.7217	Intermediate Similarity	NPD5251	Approved
0.7217	Intermediate Similarity	NPD5250	Approved
0.7217	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5169	Approved
0.7212	Intermediate Similarity	NPD5737	Approved
0.7212	Intermediate Similarity	NPD6672	Approved
0.7203	Intermediate Similarity	NPD6868	Approved
0.719	Intermediate Similarity	NPD6016	Approved
0.719	Intermediate Similarity	NPD6908	Approved
0.719	Intermediate Similarity	NPD6909	Approved
0.719	Intermediate Similarity	NPD6015	Approved
0.7184	Intermediate Similarity	NPD6409	Approved
0.7184	Intermediate Similarity	NPD7521	Approved
0.7184	Intermediate Similarity	NPD7334	Approved
0.7184	Intermediate Similarity	NPD6684	Approved
0.7184	Intermediate Similarity	NPD7146	Approved
0.7184	Intermediate Similarity	NPD5330	Approved
0.717	Intermediate Similarity	NPD8034	Phase 2
0.717	Intermediate Similarity	NPD8035	Phase 2
0.7155	Intermediate Similarity	NPD5217	Approved
0.7155	Intermediate Similarity	NPD5216	Approved
0.7155	Intermediate Similarity	NPD5215	Approved
0.7155	Intermediate Similarity	NPD5127	Approved
0.7131	Intermediate Similarity	NPD5988	Approved
0.713	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD4223	Phase 3
0.7129	Intermediate Similarity	NPD4221	Approved
0.71	Intermediate Similarity	NPD7525	Registered
0.7091	Intermediate Similarity	NPD5696	Approved
0.7091	Intermediate Similarity	NPD4225	Approved
0.7087	Intermediate Similarity	NPD5329	Approved
0.7071	Intermediate Similarity	NPD6118	Approved
0.7071	Intermediate Similarity	NPD6114	Approved
0.7071	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD6697	Approved
0.7071	Intermediate Similarity	NPD6115	Approved
0.7049	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6903	Approved
0.7043	Intermediate Similarity	NPD6686	Approved
0.7043	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD5168	Approved
0.7037	Intermediate Similarity	NPD7900	Approved
0.7037	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7516	Approved
0.7019	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4694	Approved
0.7019	Intermediate Similarity	NPD5280	Approved
0.7019	Intermediate Similarity	NPD5690	Phase 2
0.7009	Intermediate Similarity	NPD6411	Approved
0.7009	Intermediate Similarity	NPD6050	Approved
0.699	Remote Similarity	NPD3668	Phase 3
0.699	Remote Similarity	NPD4197	Approved
0.6984	Remote Similarity	NPD6033	Approved
0.6981	Remote Similarity	NPD6904	Approved
0.6981	Remote Similarity	NPD6080	Approved
0.6981	Remote Similarity	NPD6673	Approved
0.6975	Remote Similarity	NPD5167	Approved
0.6972	Remote Similarity	NPD5210	Approved
0.6972	Remote Similarity	NPD4629	Approved
0.697	Remote Similarity	NPD6116	Phase 1
0.6957	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD3573	Approved
0.6942	Remote Similarity	NPD7328	Approved
0.6942	Remote Similarity	NPD7327	Approved
0.6935	Remote Similarity	NPD8328	Phase 3
0.6916	Remote Similarity	NPD5692	Phase 3
0.6911	Remote Similarity	NPD8033	Approved
0.6893	Remote Similarity	NPD4788	Approved
0.6875	Remote Similarity	NPD6404	Discontinued
0.6869	Remote Similarity	NPD6117	Approved
0.6857	Remote Similarity	NPD4519	Discontinued
0.6857	Remote Similarity	NPD4688	Approved
0.6857	Remote Similarity	NPD4693	Phase 3
0.6857	Remote Similarity	NPD4689	Approved
0.6857	Remote Similarity	NPD5205	Approved
0.6857	Remote Similarity	NPD4138	Approved
0.6857	Remote Similarity	NPD4623	Approved
0.6857	Remote Similarity	NPD4690	Approved
0.6852	Remote Similarity	NPD7637	Suspended
0.6852	Remote Similarity	NPD5694	Approved
0.6852	Remote Similarity	NPD5693	Phase 1
0.6829	Remote Similarity	NPD8294	Approved
0.6829	Remote Similarity	NPD8377	Approved
0.6822	Remote Similarity	NPD7260	Phase 2

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