NPASS Compound

Structure

CID11710 OpenBabel06191715342D 35 38 0 0 1 0 0 0 0 0999 V2000 -3.2803 -0.0963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6121 1.2339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5341 0.5238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0022 2.9244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6886 0.9743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3069 1.5920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2813 1.5914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6883 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3790 -1.9498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8452 -1.4629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3784 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8443 1.4628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5347 -1.4624 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8449 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6901 -1.9503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2230 -1.4619 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2227 -0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6892 0.9753 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8452 1.4623 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8202 2.4361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6895 0.0005 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7680 0.7472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5344 -0.4870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0003 0.9748 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8457 2.4367 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 1.6904 -2.9612 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0986 -1.9669 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0981 0.0190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5646 1.4808 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3079 3.2797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6116 0.2595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8463 3.4111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 4 25 1 0 0 0 0 6 9 1 0 0 0 0 6 20 1 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 23 1 0 0 0 0 9 27 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 12 24 1 0 0 0 0 13 19 1 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 1 0 0 0 15 22 1 0 0 0 0 15 27 1 0 0 0 0 16 28 2 0 0 0 0 17 18 1 0 0 0 0 17 29 1 6 0 0 0 18 30 1 6 0 0 0 19 22 1 0 0 0 0 19 31 1 1 0 0 0 20 25 1 6 0 0 0 20 26 1 0 0 0 0 21 26 1 0 0 0 0 21 32 1 1 0 0 0 22 24 1 6 0 0 0 23 33 1 0 0 0 0 24 3 1 6 0 0 0 25 27 1 6 0 0 0 26 5 1 1 0 0 0 26 34 1 0 0 0 0 27 35 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.3
Volume:	506.371
LogP:	0.559
LogD:	-0.237
LogS:	-2.766
# Rotatable Bonds:	5
TPSA:	158.68
# H-Bond Aceptor:	8
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.277
Synthetic Accessibility Score:	5.517
Fsp3:	0.889
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.368
MDCK Permeability:	1.1448340046626981e-05
Pgp-inhibitor:	0.012
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.386
20% Bioavailability (F20%):	0.813
30% Bioavailability (F30%):	0.285

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.164
Plasma Protein Binding (PPB):	40.89977264404297%
Volume Distribution (VD):	0.767
Pgp-substrate:	42.41107177734375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.002
CYP1A2-substrate:	0.179
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.612
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.135
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.037
CYP3A4-inhibitor:	0.057
CYP3A4-substrate:	0.213

ADMET: Excretion

Clearance (CL):	1.984
Half-life (T1/2):	0.355

ADMET: Toxicity

hERG Blockers:	0.094
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.097
AMES Toxicity:	0.109
Rat Oral Acute Toxicity:	0.838
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.477
Carcinogencity:	0.155
Eye Corrosion:	0.006
Eye Irritation:	0.077
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC11710

Natural Product ID:	NPC11710
*Common Name:**	Turkesterone
IUPAC Name:	(2S,3R,5R,9R,10R,11R,13R,14S,17S)-2,3,11,14-tetrahydroxy-10,13-dimethyl-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-6-one
Synonyms:	Turkesterone
Standard InCHIKey:	WSBAGDDNVWTLOM-XHZKDPLLSA-N
Standard InCHI:	InChI=1S/C27H44O8/c1-23(2,33)8-7-21(32)26(5,34)20-6-9-27(35)15-11-16(28)14-10-17(29)18(30)12-24(14,3)22(15)19(31)13-25(20,27)4/h11,14,17-22,29-35H,6-10,12-13H2,1-5H3/t14-,17+,18-,19+,20-,21+,22+,24-,25+,26+,27+/m0/s1
SMILES:	O[C@@H]1C[C@]2(C)[C@H](CC[C@]2(C2=CC(=O)[C@H]3[C@]([C@@H]12)(C)C[C@H](O)[C@@H](C3)O)O)[C@]([C@@H](CCC(O)(C)C)O)(O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2087140
PubChem CID:	14376672
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

*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
NPO27472	Daiswa polyphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27472	Daiswa polyphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27472	Daiswa polyphylla	Species	Melanthiaceae	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	1
Others	6

Activity Type	# Activity
Individual Protein	4
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	Ratio	=	0.93	n.a.	PMID[468370]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FICI	=	5.19	n.a.	PMID[468370]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FICI	=	4.53	n.a.	PMID[468370]
NPT668	Individual Protein	P-glycoprotein 1	Homo sapiens	FICI	=	4.2	n.a.	PMID[468370]
NPT27	Others	Unspecified		CC50	>	700000.0	nM	PMID[468371]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	18.3	n.a.	PMID[468371]
NPT194	Organism	Dengue virus 2	Dengue virus 2	EC50	=	38150.0	nM	PMID[468371]

☑ 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 NPC11710 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	212
0.1-0.2	1324
0.2-0.3	4339
0.3-0.4	8399
0.4-0.5	12709
0.5-0.6	6833
0.6-0.7	6071
0.7-0.8	2549
0.8-0.85	193
0.85-0.9	33
0.9-0.95	7
0.95-1	28

Similarity Score	Similarity Level	Natural Product ID
0.99	High Similarity	NPC217201
0.98	High Similarity	NPC220229
0.98	High Similarity	NPC475060
0.97	High Similarity	NPC150531
0.97	High Similarity	NPC48733
0.97	High Similarity	NPC319077
0.97	High Similarity	NPC85829
0.97	High Similarity	NPC171137
0.97	High Similarity	NPC50692
0.97	High Similarity	NPC296945
0.97	High Similarity	NPC202167
0.97	High Similarity	NPC260268
0.97	High Similarity	NPC49958
0.97	High Similarity	NPC302607
0.97	High Similarity	NPC149047
0.97	High Similarity	NPC152695
0.97	High Similarity	NPC476027
0.97	High Similarity	NPC97202
0.97	High Similarity	NPC214264
0.9615	High Similarity	NPC73300
0.9615	High Similarity	NPC108721
0.9604	High Similarity	NPC83744
0.96	High Similarity	NPC204833
0.96	High Similarity	NPC209502
0.951	High Similarity	NPC329417
0.9412	High Similarity	NPC477916
0.94	High Similarity	NPC477915
0.9245	High Similarity	NPC962
0.9245	High Similarity	NPC250109
0.92	High Similarity	NPC154072
0.9151	High Similarity	NPC207251
0.9143	High Similarity	NPC76084
0.9135	High Similarity	NPC65941
0.9074	High Similarity	NPC266728
0.9074	High Similarity	NPC49492
0.9065	High Similarity	NPC317210
0.9048	High Similarity	NPC214644
0.902	High Similarity	NPC473424
0.8981	High Similarity	NPC326542
0.8942	High Similarity	NPC323834
0.8932	High Similarity	NPC191892
0.8929	High Similarity	NPC222688
0.8857	High Similarity	NPC165873
0.8829	High Similarity	NPC475041
0.88	High Similarity	NPC271195
0.8762	High Similarity	NPC166607
0.8762	High Similarity	NPC257353
0.8761	High Similarity	NPC269642
0.875	High Similarity	NPC109973
0.87	High Similarity	NPC111015
0.87	High Similarity	NPC196227
0.8667	High Similarity	NPC160843
0.8649	High Similarity	NPC471854
0.8627	High Similarity	NPC190554
0.8614	High Similarity	NPC200702
0.8596	High Similarity	NPC28532
0.8571	High Similarity	NPC311612
0.8571	High Similarity	NPC55872
0.8571	High Similarity	NPC117185
0.8571	High Similarity	NPC249187
0.8571	High Similarity	NPC247957
0.8529	High Similarity	NPC249954
0.8529	High Similarity	NPC471463
0.8515	High Similarity	NPC472976
0.8515	High Similarity	NPC472977
0.8505	High Similarity	NPC185
0.85	High Similarity	NPC116726
0.8491	Intermediate Similarity	NPC75531
0.8491	Intermediate Similarity	NPC28656
0.8491	Intermediate Similarity	NPC149124
0.8491	Intermediate Similarity	NPC72255
0.8476	Intermediate Similarity	NPC204450
0.8476	Intermediate Similarity	NPC87351
0.8476	Intermediate Similarity	NPC195290
0.8462	Intermediate Similarity	NPC15390
0.8462	Intermediate Similarity	NPC316964
0.8462	Intermediate Similarity	NPC110149
0.8455	Intermediate Similarity	NPC280782
0.8447	Intermediate Similarity	NPC18509
0.8431	Intermediate Similarity	NPC472485
0.8431	Intermediate Similarity	NPC259286
0.8431	Intermediate Similarity	NPC472932
0.8431	Intermediate Similarity	NPC473170
0.8416	Intermediate Similarity	NPC109305
0.8416	Intermediate Similarity	NPC69454
0.8407	Intermediate Similarity	NPC257457
0.8407	Intermediate Similarity	NPC311554
0.84	Intermediate Similarity	NPC48010
0.8396	Intermediate Similarity	NPC236390
0.8365	Intermediate Similarity	NPC103051
0.8362	Intermediate Similarity	NPC473979
0.835	Intermediate Similarity	NPC117133
0.835	Intermediate Similarity	NPC49371
0.8333	Intermediate Similarity	NPC8993
0.8333	Intermediate Similarity	NPC196485
0.8333	Intermediate Similarity	NPC245972
0.8333	Intermediate Similarity	NPC58370
0.8333	Intermediate Similarity	NPC144459
0.8333	Intermediate Similarity	NPC43285
0.8319	Intermediate Similarity	NPC231529
0.8318	Intermediate Similarity	NPC477812
0.8317	Intermediate Similarity	NPC155304
0.8317	Intermediate Similarity	NPC63748
0.8317	Intermediate Similarity	NPC233116
0.8317	Intermediate Similarity	NPC475806
0.8317	Intermediate Similarity	NPC473998
0.8305	Intermediate Similarity	NPC470882
0.8302	Intermediate Similarity	NPC136289
0.83	Intermediate Similarity	NPC32830
0.83	Intermediate Similarity	NPC473999
0.83	Intermediate Similarity	NPC309603
0.83	Intermediate Similarity	NPC477943
0.83	Intermediate Similarity	NPC186688
0.8288	Intermediate Similarity	NPC472002
0.8286	Intermediate Similarity	NPC218383
0.8286	Intermediate Similarity	NPC83709
0.8286	Intermediate Similarity	NPC144956
0.8273	Intermediate Similarity	NPC235077
0.8269	Intermediate Similarity	NPC320306
0.8269	Intermediate Similarity	NPC474785
0.8269	Intermediate Similarity	NPC474938
0.8252	Intermediate Similarity	NPC53565
0.8241	Intermediate Similarity	NPC60681
0.8235	Intermediate Similarity	NPC472496
0.8235	Intermediate Similarity	NPC472930
0.8235	Intermediate Similarity	NPC474736
0.823	Intermediate Similarity	NPC148458
0.823	Intermediate Similarity	NPC196931
0.8224	Intermediate Similarity	NPC26478
0.8224	Intermediate Similarity	NPC111323
0.8218	Intermediate Similarity	NPC100313
0.8218	Intermediate Similarity	NPC136801
0.8218	Intermediate Similarity	NPC134321
0.8208	Intermediate Similarity	NPC81530
0.8208	Intermediate Similarity	NPC163372
0.8208	Intermediate Similarity	NPC302537
0.82	Intermediate Similarity	NPC474668
0.82	Intermediate Similarity	NPC328539
0.8198	Intermediate Similarity	NPC472928
0.819	Intermediate Similarity	NPC477854
0.819	Intermediate Similarity	NPC197386
0.819	Intermediate Similarity	NPC10364
0.819	Intermediate Similarity	NPC114274
0.8182	Intermediate Similarity	NPC470257
0.8182	Intermediate Similarity	NPC163004
0.8174	Intermediate Similarity	NPC61520
0.8173	Intermediate Similarity	NPC477853
0.8173	Intermediate Similarity	NPC173272
0.8165	Intermediate Similarity	NPC472925
0.8165	Intermediate Similarity	NPC230541
0.8158	Intermediate Similarity	NPC55296
0.8155	Intermediate Similarity	NPC292793
0.8155	Intermediate Similarity	NPC470958
0.8155	Intermediate Similarity	NPC103527
0.8155	Intermediate Similarity	NPC280804
0.8155	Intermediate Similarity	NPC470957
0.8151	Intermediate Similarity	NPC473265
0.8137	Intermediate Similarity	NPC472978
0.8137	Intermediate Similarity	NPC168027
0.8137	Intermediate Similarity	NPC185936
0.8131	Intermediate Similarity	NPC293753
0.8131	Intermediate Similarity	NPC22388
0.8131	Intermediate Similarity	NPC308726
0.8131	Intermediate Similarity	NPC185530
0.8131	Intermediate Similarity	NPC234892
0.8131	Intermediate Similarity	NPC119601
0.8125	Intermediate Similarity	NPC71348
0.8119	Intermediate Similarity	NPC250592
0.8119	Intermediate Similarity	NPC275740
0.8119	Intermediate Similarity	NPC472973
0.8119	Intermediate Similarity	NPC1015
0.8119	Intermediate Similarity	NPC2983
0.8119	Intermediate Similarity	NPC77263
0.8119	Intermediate Similarity	NPC31985
0.8119	Intermediate Similarity	NPC86319
0.8113	Intermediate Similarity	NPC474720
0.8113	Intermediate Similarity	NPC327431
0.8113	Intermediate Similarity	NPC476274
0.8113	Intermediate Similarity	NPC127408
0.8113	Intermediate Similarity	NPC205899
0.8113	Intermediate Similarity	NPC291785
0.8108	Intermediate Similarity	NPC197428
0.81	Intermediate Similarity	NPC475740
0.8095	Intermediate Similarity	NPC161147
0.8095	Intermediate Similarity	NPC170978
0.8095	Intermediate Similarity	NPC108078
0.8095	Intermediate Similarity	NPC18319
0.8095	Intermediate Similarity	NPC107243
0.8091	Intermediate Similarity	NPC472217
0.8091	Intermediate Similarity	NPC168883
0.8091	Intermediate Similarity	NPC177064
0.8091	Intermediate Similarity	NPC472218
0.8091	Intermediate Similarity	NPC295244
0.8091	Intermediate Similarity	NPC472219
0.8087	Intermediate Similarity	NPC329736
0.8087	Intermediate Similarity	NPC251310
0.8077	Intermediate Similarity	NPC297199
0.8077	Intermediate Similarity	NPC318282
0.8077	Intermediate Similarity	NPC469995
0.8077	Intermediate Similarity	NPC472824

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 NPC11710 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1600
0.2-0.3	3929
0.3-0.4	2287
0.4-0.5	656
0.5-0.6	178
0.6-0.7	161
0.7-0.8	121
0.8-0.85	32
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8476	Intermediate Similarity	NPD5211	Phase 2
0.8447	Intermediate Similarity	NPD4755	Approved
0.8318	Intermediate Similarity	NPD5141	Approved
0.83	Intermediate Similarity	NPD5328	Approved
0.8286	Intermediate Similarity	NPD4700	Approved
0.8286	Intermediate Similarity	NPD5285	Approved
0.8286	Intermediate Similarity	NPD4696	Approved
0.8286	Intermediate Similarity	NPD5286	Approved
0.8273	Intermediate Similarity	NPD4634	Approved
0.8235	Intermediate Similarity	NPD4202	Approved
0.8208	Intermediate Similarity	NPD5223	Approved
0.8182	Intermediate Similarity	NPD6373	Approved
0.8182	Intermediate Similarity	NPD6372	Approved
0.8137	Intermediate Similarity	NPD6079	Approved
0.8131	Intermediate Similarity	NPD5225	Approved
0.8131	Intermediate Similarity	NPD5224	Approved
0.8131	Intermediate Similarity	NPD5226	Approved
0.8131	Intermediate Similarity	NPD4633	Approved
0.8073	Intermediate Similarity	NPD4768	Approved
0.8073	Intermediate Similarity	NPD6402	Approved
0.8073	Intermediate Similarity	NPD7128	Approved
0.8073	Intermediate Similarity	NPD4767	Approved
0.8073	Intermediate Similarity	NPD6675	Approved
0.8073	Intermediate Similarity	NPD5739	Approved
0.8056	Intermediate Similarity	NPD5175	Approved
0.8056	Intermediate Similarity	NPD5174	Approved
0.8056	Intermediate Similarity	NPD4754	Approved
0.8053	Intermediate Similarity	NPD4632	Approved
0.8036	Intermediate Similarity	NPD6649	Approved
0.8036	Intermediate Similarity	NPD6650	Approved
0.8	Intermediate Similarity	NPD3618	Phase 1
0.8	Intermediate Similarity	NPD4697	Phase 3
0.7965	Intermediate Similarity	NPD8297	Approved
0.7928	Intermediate Similarity	NPD4730	Approved
0.7928	Intermediate Similarity	NPD7320	Approved
0.7928	Intermediate Similarity	NPD4729	Approved
0.7928	Intermediate Similarity	NPD6899	Approved
0.7928	Intermediate Similarity	NPD6881	Approved
0.7909	Intermediate Similarity	NPD6008	Approved
0.7838	Intermediate Similarity	NPD5701	Approved
0.7838	Intermediate Similarity	NPD5697	Approved
0.783	Intermediate Similarity	NPD5221	Approved
0.783	Intermediate Similarity	NPD5222	Approved
0.783	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD6882	Approved
0.78	Intermediate Similarity	NPD3665	Phase 1
0.78	Intermediate Similarity	NPD3133	Approved
0.78	Intermediate Similarity	NPD3666	Approved
0.78	Intermediate Similarity	NPD4786	Approved
0.7797	Intermediate Similarity	NPD6319	Approved
0.7788	Intermediate Similarity	NPD7102	Approved
0.7788	Intermediate Similarity	NPD5250	Approved
0.7788	Intermediate Similarity	NPD7290	Approved
0.7788	Intermediate Similarity	NPD5251	Approved
0.7788	Intermediate Similarity	NPD6883	Approved
0.7788	Intermediate Similarity	NPD5248	Approved
0.7788	Intermediate Similarity	NPD5247	Approved
0.7788	Intermediate Similarity	NPD5249	Phase 3
0.7768	Intermediate Similarity	NPD5128	Approved
0.7768	Intermediate Similarity	NPD6011	Approved
0.7767	Intermediate Similarity	NPD4753	Phase 2
0.7757	Intermediate Similarity	NPD5173	Approved
0.7719	Intermediate Similarity	NPD6869	Approved
0.7719	Intermediate Similarity	NPD6847	Approved
0.7719	Intermediate Similarity	NPD8130	Phase 1
0.7719	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD6617	Approved
0.7699	Intermediate Similarity	NPD6014	Approved
0.7699	Intermediate Similarity	NPD6013	Approved
0.7699	Intermediate Similarity	NPD6012	Approved
0.7692	Intermediate Similarity	NPD7115	Discovery
0.7692	Intermediate Similarity	NPD6009	Approved
0.7647	Intermediate Similarity	NPD6059	Approved
0.7647	Intermediate Similarity	NPD6054	Approved
0.7632	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD5135	Approved
0.7632	Intermediate Similarity	NPD5169	Approved
0.7623	Intermediate Similarity	NPD7507	Approved
0.7615	Intermediate Similarity	NPD7640	Approved
0.7615	Intermediate Similarity	NPD7639	Approved
0.76	Intermediate Similarity	NPD4221	Approved
0.76	Intermediate Similarity	NPD3667	Approved
0.76	Intermediate Similarity	NPD4223	Phase 3
0.757	Intermediate Similarity	NPD5210	Approved
0.757	Intermediate Similarity	NPD4629	Approved
0.7565	Intermediate Similarity	NPD5217	Approved
0.7565	Intermediate Similarity	NPD5215	Approved
0.7565	Intermediate Similarity	NPD5127	Approved
0.7565	Intermediate Similarity	NPD5216	Approved
0.7549	Intermediate Similarity	NPD5329	Approved
0.7547	Intermediate Similarity	NPD6399	Phase 3
0.7523	Intermediate Similarity	NPD7638	Approved
0.7522	Intermediate Similarity	NPD6412	Phase 2
0.7521	Intermediate Similarity	NPD6370	Approved
0.7476	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7604	Phase 2
0.7451	Intermediate Similarity	NPD4197	Approved
0.744	Intermediate Similarity	NPD7319	Approved
0.7438	Intermediate Similarity	NPD6015	Approved
0.7438	Intermediate Similarity	NPD6016	Approved
0.7438	Intermediate Similarity	NPD5983	Phase 2
0.7431	Intermediate Similarity	NPD6084	Phase 2
0.7431	Intermediate Similarity	NPD6083	Phase 2
0.7404	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD7492	Approved
0.7377	Intermediate Similarity	NPD5988	Approved
0.7373	Intermediate Similarity	NPD5167	Approved
0.7339	Intermediate Similarity	NPD6336	Discontinued
0.7339	Intermediate Similarity	NPD6616	Approved
0.7333	Intermediate Similarity	NPD6335	Approved
0.7311	Intermediate Similarity	NPD6274	Approved
0.7308	Intermediate Similarity	NPD4693	Phase 3
0.7308	Intermediate Similarity	NPD4138	Approved
0.7308	Intermediate Similarity	NPD4688	Approved
0.7308	Intermediate Similarity	NPD4690	Approved
0.7308	Intermediate Similarity	NPD5205	Approved
0.7308	Intermediate Similarity	NPD4689	Approved
0.729	Intermediate Similarity	NPD7515	Phase 2
0.729	Intermediate Similarity	NPD5281	Approved
0.729	Intermediate Similarity	NPD5284	Approved
0.728	Intermediate Similarity	NPD7078	Approved
0.728	Intermediate Similarity	NPD8293	Discontinued
0.7273	Intermediate Similarity	NPD7101	Approved
0.7273	Intermediate Similarity	NPD7516	Approved
0.7273	Intermediate Similarity	NPD7100	Approved
0.725	Intermediate Similarity	NPD6317	Approved
0.7248	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7525	Registered
0.7222	Intermediate Similarity	NPD7736	Approved
0.7222	Intermediate Similarity	NPD6033	Approved
0.7207	Intermediate Similarity	NPD5696	Approved
0.7203	Intermediate Similarity	NPD6053	Discontinued
0.719	Intermediate Similarity	NPD7328	Approved
0.719	Intermediate Similarity	NPD6313	Approved
0.719	Intermediate Similarity	NPD7327	Approved
0.719	Intermediate Similarity	NPD6314	Approved
0.7184	Intermediate Similarity	NPD4788	Approved
0.7179	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7155	Intermediate Similarity	NPD5168	Approved
0.7154	Intermediate Similarity	NPD6909	Approved
0.7154	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6908	Approved
0.7143	Intermediate Similarity	NPD5280	Approved
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD5690	Phase 2
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD5330	Approved
0.7143	Intermediate Similarity	NPD4694	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7117	Intermediate Similarity	NPD7902	Approved
0.7115	Intermediate Similarity	NPD3668	Phase 3
0.7091	Intermediate Similarity	NPD5695	Phase 3
0.7018	Intermediate Similarity	NPD7632	Discontinued
0.7016	Intermediate Similarity	NPD8033	Approved
0.7009	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6903	Approved
0.7009	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7748	Approved
0.6992	Remote Similarity	NPD4522	Approved
0.6981	Remote Similarity	NPD4623	Approved
0.6981	Remote Similarity	NPD4519	Discontinued
0.6961	Remote Similarity	NPD4195	Approved
0.6944	Remote Similarity	NPD6673	Approved
0.6944	Remote Similarity	NPD6080	Approved
0.6944	Remote Similarity	NPD6904	Approved
0.6935	Remote Similarity	NPD8294	Approved
0.6935	Remote Similarity	NPD8377	Approved
0.6923	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7524	Approved
0.6905	Remote Similarity	NPD6067	Discontinued
0.6905	Remote Similarity	NPD8328	Phase 3
0.6903	Remote Similarity	NPD4225	Approved
0.69	Remote Similarity	NPD6942	Approved
0.69	Remote Similarity	NPD7339	Approved
0.6887	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD6868	Approved
0.688	Remote Similarity	NPD8379	Approved
0.688	Remote Similarity	NPD8296	Approved
0.688	Remote Similarity	NPD8378	Approved
0.688	Remote Similarity	NPD7503	Approved
0.688	Remote Similarity	NPD8335	Approved
0.688	Remote Similarity	NPD8380	Approved
0.6864	Remote Similarity	NPD6686	Approved
0.6852	Remote Similarity	NPD6672	Approved
0.6852	Remote Similarity	NPD5737	Approved
0.6847	Remote Similarity	NPD7900	Approved
0.6847	Remote Similarity	NPD6001	Approved
0.6847	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD8034	Phase 2
0.6818	Remote Similarity	NPD5693	Phase 1
0.6818	Remote Similarity	NPD8035	Phase 2
0.6807	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6371	Approved
0.6733	Remote Similarity	NPD3703	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