NPASS Compound

Structure

NPC475041 OpenBabel07101719162D 36 40 0 0 1 0 0 0 0 0999 V2000 -4.8126 -4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1727 -3.0917 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 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0522 -3.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8344 -4.5780 0.0000 C 0 0 0 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 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1945 -2.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5254 -3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2382 -2.4680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8855 -1.9328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 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 -1.2601 -2.2601 0.0000 C 0 0 1 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 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5546 -1.1896 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9074 -1.7248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 2 15 1 0 0 0 0 4 27 1 0 0 0 0 6 16 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 10 1 0 0 0 0 8 23 1 0 0 0 0 9 27 1 0 0 0 0 10 29 1 0 0 0 0 11 16 1 0 0 0 0 11 24 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 14 26 1 0 0 0 0 15 16 2 0 0 0 0 15 25 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 1 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 19 26 1 6 0 0 0 20 30 2 0 0 0 0 21 22 1 0 0 0 0 21 31 1 1 0 0 0 22 32 1 1 0 0 0 23 27 1 1 0 0 0 23 28 1 0 0 0 0 24 28 1 1 0 0 0 24 36 1 0 0 0 0 25 33 2 0 0 0 0 25 36 1 0 0 0 0 26 3 1 1 0 0 0 27 29 1 1 0 0 0 28 5 1 6 0 0 0 28 34 1 0 0 0 0 29 35 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	502.29
Volume:	518.343
LogP:	2.697
LogD:	1.312
LogS:	-4.28
# Rotatable Bonds:	2
TPSA:	124.29
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	5.68
Fsp3:	0.793
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.83
MDCK Permeability:	9.029420652950648e-06
Pgp-inhibitor:	0.094
Pgp-substrate:	0.995
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.904
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.559
Plasma Protein Binding (PPB):	63.786277770996094%
Volume Distribution (VD):	1.305
Pgp-substrate:	24.93817901611328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.27
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.688
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.744
CYP3A4-substrate:	0.71

ADMET: Excretion

Clearance (CL):	3.653
Half-life (T1/2):	0.211

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.127
Drug-inuced Liver Injury (DILI):	0.1
AMES Toxicity:	0.031
Rat Oral Acute Toxicity:	0.855
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.181
Carcinogencity:	0.843
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC475041

Natural Product ID:	NPC475041
*Common Name:**	(2R)-4-Ethyl-2-[(1R)-1-Hydroxy-1-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-Trihydroxy-10,13-Dimethyl-6-Oxo-2,3,4,5,9,11,12,15,16,17-Decahydro-1H-Cyclopenta[A]Phenanthren-17-Yl]Ethyl]-5-Methyl-2,3-Dihydropyran-6-One
IUPAC Name:	(2R)-4-ethyl-2-[(1R)-1-hydroxy-1-[(2S,3R,5R,9R,10R,13R,14S,17S)-2,3,14-trihydroxy-10,13-dimethyl-6-oxo-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-methyl-2,3-dihydropyran-6-one
Synonyms:
Standard InCHIKey:	LLXAAKCFCCZZLC-FORVDKSSSA-N
Standard InCHI:	InChI=1S/C29H42O7/c1-6-16-11-24(36-25(33)15(16)2)28(5,34)23-8-10-29(35)18-12-20(30)19-13-21(31)22(32)14-26(19,3)17(18)7-9-27(23,29)4/h12,17,19,21-24,31-32,34-35H,6-11,13-14H2,1-5H3/t17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1
SMILES:	CCC1=C(C(=O)OC(C1)C(C)(C2CCC3(C2(CCC4C3=CC(=O)C5C4(CC(C(C5)O)O)C)C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL494055
PubChem CID:	44566367
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides 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
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	flowering whole plant	n.a.	n.a.	PMID[10425119]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748375]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17539	Ajuga decumbens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17539	Ajuga decumbens	Species	Lamiaceae	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
Others	8

Activity Type	# Activity
Cell Line	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[542011]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[542011]
NPT2	Others	Unspecified		Activity	=	100.0	%	PMID[542011]
NPT2	Others	Unspecified		Activity	=	17.5	%	PMID[542011]
NPT2	Others	Unspecified		Activity	=	81.0	%	PMID[542011]
NPT2	Others	Unspecified		Activity	=	58.2	%	PMID[542011]

☑ 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 NPC475041 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	236
0.1-0.2	1350
0.2-0.3	3891
0.3-0.4	6891
0.4-0.5	12599
0.5-0.6	6934
0.6-0.7	6580
0.7-0.8	3582
0.8-0.85	438
0.85-0.9	172
0.9-0.95	22
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9732	High Similarity	NPC269642
0.9364	High Similarity	NPC962
0.9364	High Similarity	NPC250109
0.9196	High Similarity	NPC49492
0.9196	High Similarity	NPC190286
0.9196	High Similarity	NPC266728
0.9145	High Similarity	NPC293112
0.9138	High Similarity	NPC469789
0.913	High Similarity	NPC46570
0.906	High Similarity	NPC172154
0.906	High Similarity	NPC81736
0.9052	High Similarity	NPC107493
0.9043	High Similarity	NPC79579
0.9035	High Similarity	NPC153440
0.9027	High Similarity	NPC176840
0.9018	High Similarity	NPC317210
0.8991	High Similarity	NPC475060
0.8991	High Similarity	NPC220229
0.8974	High Similarity	NPC11895
0.8974	High Similarity	NPC473979
0.8966	High Similarity	NPC67569
0.8957	High Similarity	NPC270850
0.8957	High Similarity	NPC5292
0.8957	High Similarity	NPC305260
0.8938	High Similarity	NPC326542
0.8929	High Similarity	NPC207251
0.8929	High Similarity	NPC236217
0.8919	High Similarity	NPC76084
0.8917	High Similarity	NPC231529
0.8909	High Similarity	NPC217201
0.8899	High Similarity	NPC85829
0.8899	High Similarity	NPC150531
0.8899	High Similarity	NPC97202
0.8899	High Similarity	NPC296945
0.8899	High Similarity	NPC260268
0.8899	High Similarity	NPC48733
0.8899	High Similarity	NPC476027
0.8899	High Similarity	NPC319077
0.8899	High Similarity	NPC149047
0.8899	High Similarity	NPC50692
0.8899	High Similarity	NPC49958
0.8899	High Similarity	NPC302607
0.8899	High Similarity	NPC202167
0.8899	High Similarity	NPC214264
0.8899	High Similarity	NPC171137
0.8899	High Similarity	NPC152695
0.8898	High Similarity	NPC8369
0.8898	High Similarity	NPC8374
0.8889	High Similarity	NPC23786
0.8889	High Similarity	NPC170538
0.8889	High Similarity	NPC470265
0.8889	High Similarity	NPC222688
0.8879	High Similarity	NPC268530
0.8879	High Similarity	NPC109973
0.8879	High Similarity	NPC474370
0.8879	High Similarity	NPC154491
0.8879	High Similarity	NPC474585
0.886	High Similarity	NPC196931
0.8829	High Similarity	NPC11710
0.8824	High Similarity	NPC473635
0.8818	High Similarity	NPC83744
0.8807	High Similarity	NPC209502
0.8807	High Similarity	NPC204833
0.8803	High Similarity	NPC159456
0.8803	High Similarity	NPC4021
0.8793	High Similarity	NPC230513
0.8793	High Similarity	NPC264954
0.8783	High Similarity	NPC55296
0.8772	High Similarity	NPC474181
0.8772	High Similarity	NPC147912
0.8772	High Similarity	NPC67259
0.877	High Similarity	NPC471855
0.875	High Similarity	NPC470882
0.875	High Similarity	NPC37116
0.8739	High Similarity	NPC329417
0.8739	High Similarity	NPC469790
0.8729	High Similarity	NPC28532
0.8729	High Similarity	NPC88326
0.8729	High Similarity	NPC153700
0.8727	High Similarity	NPC323834
0.8718	High Similarity	NPC476961
0.8718	High Similarity	NPC251226
0.8707	High Similarity	NPC311554
0.8707	High Similarity	NPC257457
0.8707	High Similarity	NPC50774
0.8707	High Similarity	NPC709
0.8689	High Similarity	NPC173347
0.8684	High Similarity	NPC194100
0.8684	High Similarity	NPC25909
0.8678	High Similarity	NPC311534
0.8649	High Similarity	NPC230541
0.8649	High Similarity	NPC477916
0.8649	High Similarity	NPC144459
0.8632	High Similarity	NPC61520
0.8632	High Similarity	NPC42673
0.8624	High Similarity	NPC477915
0.8621	High Similarity	NPC286528
0.8621	High Similarity	NPC20302
0.8621	High Similarity	NPC473968
0.8621	High Similarity	NPC284068
0.8621	High Similarity	NPC140055
0.8621	High Similarity	NPC471854
0.8621	High Similarity	NPC470492
0.8621	High Similarity	NPC167606
0.8609	High Similarity	NPC284915
0.8607	High Similarity	NPC471407
0.8596	High Similarity	NPC472002
0.8596	High Similarity	NPC280782
0.8596	High Similarity	NPC269530
0.8595	High Similarity	NPC473265
0.8595	High Similarity	NPC473253
0.8595	High Similarity	NPC287423
0.8584	High Similarity	NPC197428
0.8571	High Similarity	NPC189075
0.8571	High Similarity	NPC88701
0.8571	High Similarity	NPC275539
0.8559	High Similarity	NPC231530
0.8559	High Similarity	NPC278628
0.8559	High Similarity	NPC102352
0.8547	High Similarity	NPC329736
0.8534	High Similarity	NPC64318
0.8534	High Similarity	NPC148458
0.8525	High Similarity	NPC473888
0.8522	High Similarity	NPC108721
0.8522	High Similarity	NPC73300
0.8512	High Similarity	NPC120994
0.8512	High Similarity	NPC203702
0.8509	High Similarity	NPC97939
0.8509	High Similarity	NPC132790
0.8509	High Similarity	NPC247031
0.8509	High Similarity	NPC188738
0.8509	High Similarity	NPC469656
0.8509	High Similarity	NPC469655
0.8509	High Similarity	NPC100329
0.8509	High Similarity	NPC474846
0.85	High Similarity	NPC204812
0.85	High Similarity	NPC27363
0.85	High Similarity	NPC67251
0.8496	Intermediate Similarity	NPC141350
0.8496	Intermediate Similarity	NPC173905
0.8496	Intermediate Similarity	NPC5475
0.8496	Intermediate Similarity	NPC284828
0.8496	Intermediate Similarity	NPC472216
0.8487	Intermediate Similarity	NPC310511
0.8482	Intermediate Similarity	NPC67321
0.8482	Intermediate Similarity	NPC110496
0.8482	Intermediate Similarity	NPC3316
0.8482	Intermediate Similarity	NPC144854
0.8482	Intermediate Similarity	NPC187435
0.8475	Intermediate Similarity	NPC473270
0.8475	Intermediate Similarity	NPC476529
0.8475	Intermediate Similarity	NPC473203
0.8475	Intermediate Similarity	NPC475775
0.8468	Intermediate Similarity	NPC149124
0.8468	Intermediate Similarity	NPC28656
0.8468	Intermediate Similarity	NPC75531
0.8462	Intermediate Similarity	NPC470959
0.8462	Intermediate Similarity	NPC470493
0.8462	Intermediate Similarity	NPC473590
0.8462	Intermediate Similarity	NPC312824
0.8462	Intermediate Similarity	NPC183580
0.8462	Intermediate Similarity	NPC469684
0.8462	Intermediate Similarity	NPC476965
0.8455	Intermediate Similarity	NPC476966
0.8455	Intermediate Similarity	NPC470880
0.8455	Intermediate Similarity	NPC136289
0.8455	Intermediate Similarity	NPC22388
0.8455	Intermediate Similarity	NPC473593
0.8448	Intermediate Similarity	NPC178289
0.8448	Intermediate Similarity	NPC243354
0.844	Intermediate Similarity	NPC218383
0.844	Intermediate Similarity	NPC154072
0.8435	Intermediate Similarity	NPC191620
0.8435	Intermediate Similarity	NPC476163
0.8435	Intermediate Similarity	NPC126691
0.843	Intermediate Similarity	NPC241456
0.843	Intermediate Similarity	NPC32868
0.843	Intermediate Similarity	NPC470922
0.843	Intermediate Similarity	NPC318135
0.843	Intermediate Similarity	NPC476729
0.843	Intermediate Similarity	NPC473255
0.8421	Intermediate Similarity	NPC478211
0.8421	Intermediate Similarity	NPC473627
0.8407	Intermediate Similarity	NPC192813
0.8407	Intermediate Similarity	NPC472218
0.8407	Intermediate Similarity	NPC472825
0.8407	Intermediate Similarity	NPC277017
0.8407	Intermediate Similarity	NPC472219
0.8407	Intermediate Similarity	NPC154608
0.8407	Intermediate Similarity	NPC472217
0.8407	Intermediate Similarity	NPC94529
0.8407	Intermediate Similarity	NPC65941
0.8403	Intermediate Similarity	NPC107338
0.8403	Intermediate Similarity	NPC476962
0.8403	Intermediate Similarity	NPC109607
0.84	Intermediate Similarity	NPC298783
0.84	Intermediate Similarity	NPC104585
0.84	Intermediate Similarity	NPC225385
0.84	Intermediate Similarity	NPC157817
0.8393	Intermediate Similarity	NPC60681

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 NPC475041 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	203
0.1-0.2	1535
0.2-0.3	3605
0.3-0.4	2420
0.4-0.5	808
0.5-0.6	265
0.6-0.7	148
0.7-0.8	141
0.8-0.85	24
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8621	High Similarity	NPD7115	Discovery
0.8362	Intermediate Similarity	NPD4632	Approved
0.8361	Intermediate Similarity	NPD7507	Approved
0.8273	Intermediate Similarity	NPD7639	Approved
0.8273	Intermediate Similarity	NPD7640	Approved
0.823	Intermediate Similarity	NPD6008	Approved
0.823	Intermediate Similarity	NPD6402	Approved
0.823	Intermediate Similarity	NPD6675	Approved
0.823	Intermediate Similarity	NPD5739	Approved
0.823	Intermediate Similarity	NPD7128	Approved
0.8182	Intermediate Similarity	NPD7638	Approved
0.8174	Intermediate Similarity	NPD6372	Approved
0.8174	Intermediate Similarity	NPD6373	Approved
0.816	Intermediate Similarity	NPD7319	Approved
0.812	Intermediate Similarity	NPD8297	Approved
0.8099	Intermediate Similarity	NPD6319	Approved
0.8087	Intermediate Similarity	NPD6881	Approved
0.8087	Intermediate Similarity	NPD6899	Approved
0.8087	Intermediate Similarity	NPD7320	Approved
0.8034	Intermediate Similarity	NPD6649	Approved
0.8034	Intermediate Similarity	NPD6650	Approved
0.8	Intermediate Similarity	NPD6009	Approved
0.8	Intermediate Similarity	NPD5701	Approved
0.8	Intermediate Similarity	NPD5697	Approved
0.7966	Intermediate Similarity	NPD6053	Discontinued
0.7949	Intermediate Similarity	NPD7290	Approved
0.7949	Intermediate Similarity	NPD7102	Approved
0.7949	Intermediate Similarity	NPD6883	Approved
0.7931	Intermediate Similarity	NPD6011	Approved
0.7903	Intermediate Similarity	NPD7604	Phase 2
0.7886	Intermediate Similarity	NPD5983	Phase 2
0.7881	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD6869	Approved
0.7881	Intermediate Similarity	NPD6847	Approved
0.7881	Intermediate Similarity	NPD8130	Phase 1
0.7881	Intermediate Similarity	NPD6617	Approved
0.7869	Intermediate Similarity	NPD7516	Approved
0.7863	Intermediate Similarity	NPD6012	Approved
0.7863	Intermediate Similarity	NPD6014	Approved
0.7863	Intermediate Similarity	NPD6013	Approved
0.7863	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7845	Intermediate Similarity	NPD6412	Phase 2
0.784	Intermediate Similarity	NPD7492	Approved
0.7815	Intermediate Similarity	NPD6882	Approved
0.7807	Intermediate Similarity	NPD5211	Phase 2
0.7805	Intermediate Similarity	NPD6054	Approved
0.7805	Intermediate Similarity	NPD6059	Approved
0.7795	Intermediate Similarity	NPD7736	Approved
0.7787	Intermediate Similarity	NPD7327	Approved
0.7787	Intermediate Similarity	NPD7328	Approved
0.7778	Intermediate Similarity	NPD6616	Approved
0.7778	Intermediate Similarity	NPD6336	Discontinued
0.7768	Intermediate Similarity	NPD4755	Approved
0.7742	Intermediate Similarity	NPD7503	Approved
0.7742	Intermediate Similarity	NPD8033	Approved
0.7727	Intermediate Similarity	NPD6399	Phase 3
0.7717	Intermediate Similarity	NPD8293	Discontinued
0.7717	Intermediate Similarity	NPD7078	Approved
0.768	Intermediate Similarity	NPD6370	Approved
0.7672	Intermediate Similarity	NPD5141	Approved
0.7661	Intermediate Similarity	NPD8294	Approved
0.7661	Intermediate Similarity	NPD8377	Approved
0.7652	Intermediate Similarity	NPD7632	Discontinued
0.7647	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4634	Approved
0.7632	Intermediate Similarity	NPD5286	Approved
0.7632	Intermediate Similarity	NPD4700	Approved
0.7632	Intermediate Similarity	NPD4696	Approved
0.7632	Intermediate Similarity	NPD5285	Approved
0.7627	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD5328	Approved
0.7611	Intermediate Similarity	NPD6083	Phase 2
0.7611	Intermediate Similarity	NPD6084	Phase 2
0.76	Intermediate Similarity	NPD8335	Approved
0.76	Intermediate Similarity	NPD8380	Approved
0.76	Intermediate Similarity	NPD8379	Approved
0.76	Intermediate Similarity	NPD8378	Approved
0.76	Intermediate Similarity	NPD6016	Approved
0.76	Intermediate Similarity	NPD6015	Approved
0.76	Intermediate Similarity	NPD8296	Approved
0.7568	Intermediate Similarity	NPD4202	Approved
0.7565	Intermediate Similarity	NPD5223	Approved
0.7544	Intermediate Similarity	NPD4225	Approved
0.754	Intermediate Similarity	NPD5988	Approved
0.75	Intermediate Similarity	NPD5225	Approved
0.75	Intermediate Similarity	NPD4633	Approved
0.75	Intermediate Similarity	NPD6371	Approved
0.75	Intermediate Similarity	NPD5226	Approved
0.75	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD5224	Approved
0.748	Intermediate Similarity	NPD6274	Approved
0.7479	Intermediate Similarity	NPD6686	Approved
0.7477	Intermediate Similarity	NPD6079	Approved
0.7456	Intermediate Similarity	NPD7902	Approved
0.744	Intermediate Similarity	NPD7101	Approved
0.744	Intermediate Similarity	NPD7100	Approved
0.7436	Intermediate Similarity	NPD4754	Approved
0.7436	Intermediate Similarity	NPD5175	Approved
0.7436	Intermediate Similarity	NPD5174	Approved
0.7434	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6317	Approved
0.7395	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5696	Approved
0.7385	Intermediate Similarity	NPD6033	Approved
0.7368	Intermediate Similarity	NPD4697	Phase 3
0.7364	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD6314	Approved
0.736	Intermediate Similarity	NPD6313	Approved
0.7345	Intermediate Similarity	NPD7748	Approved
0.7344	Intermediate Similarity	NPD8328	Phase 3
0.7339	Intermediate Similarity	NPD7521	Approved
0.7339	Intermediate Similarity	NPD7334	Approved
0.7339	Intermediate Similarity	NPD5330	Approved
0.7339	Intermediate Similarity	NPD7146	Approved
0.7339	Intermediate Similarity	NPD6409	Approved
0.7339	Intermediate Similarity	NPD3618	Phase 1
0.7339	Intermediate Similarity	NPD6684	Approved
0.7323	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD6908	Approved
0.7323	Intermediate Similarity	NPD8513	Phase 3
0.7323	Intermediate Similarity	NPD6909	Approved
0.7321	Intermediate Similarity	NPD7515	Phase 2
0.7321	Intermediate Similarity	NPD5693	Phase 1
0.7317	Intermediate Similarity	NPD8133	Approved
0.7311	Intermediate Similarity	NPD4768	Approved
0.7311	Intermediate Similarity	NPD4767	Approved
0.7281	Intermediate Similarity	NPD5695	Phase 3
0.7273	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD5221	Approved
0.7217	Intermediate Similarity	NPD5222	Approved
0.7207	Intermediate Similarity	NPD6903	Approved
0.7193	Intermediate Similarity	NPD7900	Approved
0.7193	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4730	Approved
0.719	Intermediate Similarity	NPD5128	Approved
0.719	Intermediate Similarity	NPD4729	Approved
0.7188	Intermediate Similarity	NPD8516	Approved
0.7188	Intermediate Similarity	NPD8515	Approved
0.7188	Intermediate Similarity	NPD8517	Approved
0.7168	Intermediate Similarity	NPD5284	Approved
0.7168	Intermediate Similarity	NPD8034	Phase 2
0.7168	Intermediate Similarity	NPD8035	Phase 2
0.7168	Intermediate Similarity	NPD5281	Approved
0.7156	Intermediate Similarity	NPD3666	Approved
0.7156	Intermediate Similarity	NPD3133	Approved
0.7156	Intermediate Similarity	NPD4786	Approved
0.7156	Intermediate Similarity	NPD3665	Phase 1
0.7155	Intermediate Similarity	NPD5173	Approved
0.7143	Intermediate Similarity	NPD6673	Approved
0.7143	Intermediate Similarity	NPD4753	Phase 2
0.7143	Intermediate Similarity	NPD6904	Approved
0.7143	Intermediate Similarity	NPD6080	Approved
0.7119	Intermediate Similarity	NPD5344	Discontinued
0.709	Intermediate Similarity	NPD7260	Phase 2
0.708	Intermediate Similarity	NPD5785	Approved
0.7077	Intermediate Similarity	NPD6067	Discontinued
0.7073	Intermediate Similarity	NPD5251	Approved
0.7073	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5135	Approved
0.7073	Intermediate Similarity	NPD5250	Approved
0.7073	Intermediate Similarity	NPD5248	Approved
0.7073	Intermediate Similarity	NPD5249	Phase 3
0.7073	Intermediate Similarity	NPD5169	Approved
0.7073	Intermediate Similarity	NPD5247	Approved
0.7063	Intermediate Similarity	NPD6868	Approved
0.7054	Intermediate Similarity	NPD6672	Approved
0.7054	Intermediate Similarity	NPD5737	Approved
0.7043	Intermediate Similarity	NPD6001	Approved
0.7016	Intermediate Similarity	NPD5216	Approved
0.7016	Intermediate Similarity	NPD5217	Approved
0.7016	Intermediate Similarity	NPD5215	Approved
0.7016	Intermediate Similarity	NPD5127	Approved
0.7008	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6051	Approved
0.6983	Remote Similarity	NPD4629	Approved
0.6983	Remote Similarity	NPD5210	Approved
0.6972	Remote Similarity	NPD4223	Phase 3
0.6972	Remote Similarity	NPD4221	Approved
0.6972	Remote Similarity	NPD3667	Approved
0.6967	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD3573	Approved
0.6937	Remote Similarity	NPD5329	Approved
0.6937	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6698	Approved
0.693	Remote Similarity	NPD46	Approved
0.6923	Remote Similarity	NPD6921	Approved
0.6903	Remote Similarity	NPD5208	Approved
0.688	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6098	Approved
0.6875	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6050	Approved
0.685	Remote Similarity	NPD5167	Approved
0.6847	Remote Similarity	NPD4197	Approved
0.6814	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7524	Approved
0.681	Remote Similarity	NPD5778	Approved
0.681	Remote Similarity	NPD5779	Approved
0.6791	Remote Similarity	NPD8074	Phase 3
0.6788	Remote Similarity	NPD6845	Suspended

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