NPASS Compound

Structure

NPC164999 OpenBabel07101719132D 31 33 0 0 1 0 0 0 0 0999 V2000 -8.7466 1.2273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5656 -0.4953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7576 1.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7631 1.5409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1808 -0.6499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5765 -0.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5820 -0.1817 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 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2026 -0.8578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8717 -1.6009 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 -8.1588 0.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1643 0.5228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1753 0.7319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 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 -4.1808 0.8364 0.0000 C 0 0 2 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 -0.8660 0.5000 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 -3.5116 0.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8499 -1.3930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 2 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 20 4 1 1 0 0 0 20 24 1 0 0 0 0 21 27 1 6 0 0 0 22 30 1 6 0 0 0 23 10 1 1 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 28 1 1 0 0 0 25 28 1 1 0 0 0 26 27 1 0 0 0 0 26 31 2 0 0 0 0 27 5 1 6 0 0 0 28 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.36
Volume:	488.272
LogP:	5.448
LogD:	5.22
LogS:	-5.366
# Rotatable Bonds:	8
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	4.779
Fsp3:	0.893
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.696
MDCK Permeability:	1.3895990377932321e-05
Pgp-inhibitor:	0.916
Pgp-substrate:	0.318
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.05

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.324
Plasma Protein Binding (PPB):	94.32115173339844%
Volume Distribution (VD):	1.006
Pgp-substrate:	1.8309218883514404%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.543
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.907
CYP2C9-inhibitor:	0.201
CYP2C9-substrate:	0.094
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.859
CYP3A4-substrate:	0.714

ADMET: Excretion

Clearance (CL):	10.962
Half-life (T1/2):	0.181

ADMET: Toxicity

hERG Blockers:	0.052
Human Hepatotoxicity (H-HT):	0.254
Drug-inuced Liver Injury (DILI):	0.378
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.723
Maximum Recommended Daily Dose:	0.333
Skin Sensitization:	0.456
Carcinogencity:	0.262
Eye Corrosion:	0.439
Eye Irritation:	0.337
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC164999

Natural Product ID:	NPC164999
*Common Name:**	3-Beta,11-Dihydroxy-24-Methylene-9,11-Secocholestan-9-One
IUPAC Name:	(2S,4aS,6S,8aS)-6-hydroxy-2-[(1S,2R,3R)-2-(2-hydroxyethyl)-2-methyl-3-[(2R)-6-methyl-5-methylideneheptan-2-yl]cyclopentyl]-8a-methyl-2,3,4,4a,5,6,7,8-octahydronaphthalen-1-one
Synonyms:
Standard InCHIKey:	XYHLUHZFBHYCOX-XUODJTAMSA-N
Standard InCHI:	InChI=1S/C28H48O3/c1-18(2)19(3)7-8-20(4)24-11-12-25(28(24,6)15-16-29)23-10-9-21-17-22(30)13-14-27(21,5)26(23)31/h18,20-25,29-30H,3,7-17H2,1-2,4-6H3/t20-,21+,22+,23+,24-,25+,27+,28-/m1/s1
SMILES:	CC(C)C(=C)CC[C@@H](C)[C@H]1CC[C@@H]([C@@H]2CC[C@H]3C[C@H](CC[C@]3(C)C2=O)O)[C@]1(C)CCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL496640
PubChem CID:	44583845
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

*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
NPO15548	Sinularia leptoclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724859]
NPO7825	Sinularia lochmodes	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724859]
NPO15548	Sinularia leptoclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7825	Sinularia lochmodes	Species	Alcyoniidae	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
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	8.2	ug.mL-1	PMID[508831]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	9.8	ug.mL-1	PMID[508831]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	11.3	ug.mL-1	PMID[508831]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	9.2	ug.mL-1	PMID[508831]

☑ 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 NPC164999 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	153
0.1-0.2	1498
0.2-0.3	6781
0.3-0.4	15879
0.4-0.5	6346
0.5-0.6	5979
0.6-0.7	4177
0.7-0.8	1610
0.8-0.85	227
0.85-0.9	46
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9136	High Similarity	NPC4643
0.9136	High Similarity	NPC57469
0.9114	High Similarity	NPC472743
0.9114	High Similarity	NPC475726
0.9	High Similarity	NPC474233
0.9	High Similarity	NPC146683
0.9	High Similarity	NPC474482
0.9	High Similarity	NPC475745
0.8889	High Similarity	NPC76518
0.8889	High Similarity	NPC292553
0.8875	High Similarity	NPC476082
0.8875	High Similarity	NPC118800
0.8875	High Similarity	NPC278648
0.8846	High Similarity	NPC201459
0.8795	High Similarity	NPC131470
0.8795	High Similarity	NPC143767
0.8795	High Similarity	NPC328539
0.878	High Similarity	NPC472738
0.8765	High Similarity	NPC74595
0.8765	High Similarity	NPC221758
0.8765	High Similarity	NPC59453
0.8765	High Similarity	NPC264665
0.875	High Similarity	NPC477858
0.875	High Similarity	NPC145143
0.869	High Similarity	NPC86319
0.869	High Similarity	NPC275740
0.8675	High Similarity	NPC472495
0.8675	High Similarity	NPC153604
0.8675	High Similarity	NPC472497
0.8675	High Similarity	NPC174619
0.8659	High Similarity	NPC264317
0.8659	High Similarity	NPC202868
0.8659	High Similarity	NPC294438
0.8642	High Similarity	NPC471036
0.8642	High Similarity	NPC472498
0.8642	High Similarity	NPC291320
0.8625	High Similarity	NPC103754
0.8625	High Similarity	NPC474484
0.8605	High Similarity	NPC224060
0.8605	High Similarity	NPC244356
0.859	High Similarity	NPC106078
0.8588	High Similarity	NPC183283
0.8571	High Similarity	NPC53911
0.8571	High Similarity	NPC193360
0.8571	High Similarity	NPC472739
0.8571	High Similarity	NPC474719
0.8554	High Similarity	NPC72133
0.8554	High Similarity	NPC51014
0.8554	High Similarity	NPC145879
0.8554	High Similarity	NPC474732
0.8554	High Similarity	NPC2783
0.8554	High Similarity	NPC31564
0.8554	High Similarity	NPC98236
0.8554	High Similarity	NPC269396
0.8554	High Similarity	NPC474778
0.8554	High Similarity	NPC474733
0.8554	High Similarity	NPC12774
0.8537	High Similarity	NPC214043
0.8537	High Similarity	NPC82902
0.8537	High Similarity	NPC85774
0.8519	High Similarity	NPC151519
0.8519	High Similarity	NPC110780
0.8488	Intermediate Similarity	NPC63748
0.8488	Intermediate Similarity	NPC185936
0.8488	Intermediate Similarity	NPC168027
0.8471	Intermediate Similarity	NPC309603
0.8471	Intermediate Similarity	NPC473999
0.8471	Intermediate Similarity	NPC186688
0.8462	Intermediate Similarity	NPC472486
0.8462	Intermediate Similarity	NPC472487
0.8452	Intermediate Similarity	NPC142361
0.8452	Intermediate Similarity	NPC259009
0.8452	Intermediate Similarity	NPC264005
0.8452	Intermediate Similarity	NPC58063
0.8452	Intermediate Similarity	NPC141292
0.8452	Intermediate Similarity	NPC269360
0.8452	Intermediate Similarity	NPC475740
0.8452	Intermediate Similarity	NPC474684
0.8452	Intermediate Similarity	NPC33768
0.8442	Intermediate Similarity	NPC102313
0.8442	Intermediate Similarity	NPC199316
0.8434	Intermediate Similarity	NPC471034
0.8434	Intermediate Similarity	NPC469948
0.8434	Intermediate Similarity	NPC190704
0.8434	Intermediate Similarity	NPC474218
0.8434	Intermediate Similarity	NPC470574
0.8434	Intermediate Similarity	NPC471224
0.8421	Intermediate Similarity	NPC151018
0.8421	Intermediate Similarity	NPC58057
0.8421	Intermediate Similarity	NPC320549
0.8421	Intermediate Similarity	NPC156277
0.8415	Intermediate Similarity	NPC175410
0.8415	Intermediate Similarity	NPC245866
0.8409	Intermediate Similarity	NPC266431
0.8391	Intermediate Similarity	NPC477520
0.8391	Intermediate Similarity	NPC69454
0.8391	Intermediate Similarity	NPC294263
0.8372	Intermediate Similarity	NPC180849
0.8372	Intermediate Similarity	NPC126993
0.8372	Intermediate Similarity	NPC46758
0.8372	Intermediate Similarity	NPC100313
0.8372	Intermediate Similarity	NPC80401
0.8354	Intermediate Similarity	NPC221420
0.8354	Intermediate Similarity	NPC472746
0.8353	Intermediate Similarity	NPC471722
0.8353	Intermediate Similarity	NPC16377
0.8353	Intermediate Similarity	NPC328313
0.8353	Intermediate Similarity	NPC146937
0.8353	Intermediate Similarity	NPC471900
0.8353	Intermediate Similarity	NPC292491
0.8353	Intermediate Similarity	NPC310752
0.8353	Intermediate Similarity	NPC471724
0.8333	Intermediate Similarity	NPC28252
0.8333	Intermediate Similarity	NPC20688
0.8333	Intermediate Similarity	NPC125767
0.8333	Intermediate Similarity	NPC21220
0.8333	Intermediate Similarity	NPC469994
0.8333	Intermediate Similarity	NPC70661
0.8333	Intermediate Similarity	NPC94755
0.8333	Intermediate Similarity	NPC55309
0.8333	Intermediate Similarity	NPC155011
0.8313	Intermediate Similarity	NPC473246
0.8312	Intermediate Similarity	NPC232112
0.8295	Intermediate Similarity	NPC166906
0.8295	Intermediate Similarity	NPC303863
0.8293	Intermediate Similarity	NPC46881
0.8276	Intermediate Similarity	NPC475806
0.8276	Intermediate Similarity	NPC473998
0.8276	Intermediate Similarity	NPC211403
0.8276	Intermediate Similarity	NPC476168
0.8276	Intermediate Similarity	NPC272746
0.8276	Intermediate Similarity	NPC198242
0.8256	Intermediate Similarity	NPC213832
0.8256	Intermediate Similarity	NPC268406
0.8256	Intermediate Similarity	NPC220498
0.8256	Intermediate Similarity	NPC76879
0.8256	Intermediate Similarity	NPC477943
0.8256	Intermediate Similarity	NPC474245
0.8256	Intermediate Similarity	NPC475921
0.8256	Intermediate Similarity	NPC57954
0.8256	Intermediate Similarity	NPC474704
0.8256	Intermediate Similarity	NPC26959
0.8256	Intermediate Similarity	NPC31985
0.8256	Intermediate Similarity	NPC1015
0.8256	Intermediate Similarity	NPC32830
0.8256	Intermediate Similarity	NPC128496
0.825	Intermediate Similarity	NPC185465
0.8235	Intermediate Similarity	NPC233836
0.8235	Intermediate Similarity	NPC165895
0.8235	Intermediate Similarity	NPC187376
0.8235	Intermediate Similarity	NPC474174
0.8235	Intermediate Similarity	NPC317590
0.8235	Intermediate Similarity	NPC90652
0.8235	Intermediate Similarity	NPC251808
0.8235	Intermediate Similarity	NPC159046
0.8228	Intermediate Similarity	NPC5767
0.8228	Intermediate Similarity	NPC475742
0.8228	Intermediate Similarity	NPC20466
0.8222	Intermediate Similarity	NPC170978
0.8222	Intermediate Similarity	NPC111187
0.8222	Intermediate Similarity	NPC190554
0.8222	Intermediate Similarity	NPC190080
0.8214	Intermediate Similarity	NPC201655
0.8214	Intermediate Similarity	NPC102292
0.8214	Intermediate Similarity	NPC474083
0.8205	Intermediate Similarity	NPC254340
0.8205	Intermediate Similarity	NPC133922
0.8202	Intermediate Similarity	NPC98639
0.8202	Intermediate Similarity	NPC263135
0.8202	Intermediate Similarity	NPC470016
0.8202	Intermediate Similarity	NPC288906
0.8202	Intermediate Similarity	NPC259286
0.8202	Intermediate Similarity	NPC317586
0.8193	Intermediate Similarity	NPC471037
0.8182	Intermediate Similarity	NPC477855
0.8182	Intermediate Similarity	NPC59350
0.8182	Intermediate Similarity	NPC475255
0.8182	Intermediate Similarity	NPC59170
0.8182	Intermediate Similarity	NPC472496
0.8182	Intermediate Similarity	NPC181594
0.8182	Intermediate Similarity	NPC111234
0.8182	Intermediate Similarity	NPC12722
0.8182	Intermediate Similarity	NPC144739
0.8171	Intermediate Similarity	NPC328264
0.8171	Intermediate Similarity	NPC164210
0.8161	Intermediate Similarity	NPC48010
0.8161	Intermediate Similarity	NPC85173
0.8161	Intermediate Similarity	NPC169933
0.8161	Intermediate Similarity	NPC191684
0.8158	Intermediate Similarity	NPC131892
0.8158	Intermediate Similarity	NPC213178
0.8158	Intermediate Similarity	NPC6120
0.8158	Intermediate Similarity	NPC327728
0.8158	Intermediate Similarity	NPC475952
0.8148	Intermediate Similarity	NPC192744
0.8148	Intermediate Similarity	NPC215843
0.8148	Intermediate Similarity	NPC320144
0.814	Intermediate Similarity	NPC242864
0.814	Intermediate Similarity	NPC470417
0.814	Intermediate Similarity	NPC4309

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 NPC164999 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	2014
0.2-0.3	4303
0.3-0.4	1824
0.4-0.5	424
0.5-0.6	149
0.6-0.7	130
0.7-0.8	131
0.8-0.85	22
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8916	High Similarity	NPD5328	Approved
0.8765	High Similarity	NPD4786	Approved
0.8706	High Similarity	NPD6079	Approved
0.8659	High Similarity	NPD7520	Clinical (unspecified phase)
0.8519	High Similarity	NPD3667	Approved
0.8421	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD4788	Approved
0.8333	Intermediate Similarity	NPD3618	Phase 1
0.8158	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD4697	Phase 3
0.8111	Intermediate Similarity	NPD5221	Approved
0.8111	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8111	Intermediate Similarity	NPD5222	Approved
0.8108	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8101	Intermediate Similarity	NPD3703	Phase 2
0.8095	Intermediate Similarity	NPD3133	Approved
0.8095	Intermediate Similarity	NPD3665	Phase 1
0.8095	Intermediate Similarity	NPD3666	Approved
0.8022	Intermediate Similarity	NPD5173	Approved
0.8022	Intermediate Similarity	NPD4755	Approved
0.7978	Intermediate Similarity	NPD4202	Approved
0.7975	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD8034	Phase 2
0.7865	Intermediate Similarity	NPD8035	Phase 2
0.7849	Intermediate Similarity	NPD5285	Approved
0.7849	Intermediate Similarity	NPD5286	Approved
0.7849	Intermediate Similarity	NPD4700	Approved
0.7849	Intermediate Similarity	NPD4696	Approved
0.7821	Intermediate Similarity	NPD4245	Approved
0.7821	Intermediate Similarity	NPD4244	Approved
0.7821	Intermediate Similarity	NPD4789	Approved
0.7792	Intermediate Similarity	NPD5360	Phase 3
0.7792	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6399	Phase 3
0.7778	Intermediate Similarity	NPD6117	Approved
0.7766	Intermediate Similarity	NPD5223	Approved
0.7701	Intermediate Similarity	NPD5279	Phase 3
0.7692	Intermediate Similarity	NPD3698	Phase 2
0.7684	Intermediate Similarity	NPD5224	Approved
0.7684	Intermediate Similarity	NPD5211	Phase 2
0.7684	Intermediate Similarity	NPD5225	Approved
0.7684	Intermediate Similarity	NPD4633	Approved
0.7684	Intermediate Similarity	NPD5226	Approved
0.7683	Intermediate Similarity	NPD6116	Phase 1
0.7674	Intermediate Similarity	NPD3668	Phase 3
0.7654	Intermediate Similarity	NPD7339	Approved
0.7654	Intermediate Similarity	NPD6942	Approved
0.7647	Intermediate Similarity	NPD4223	Phase 3
0.7647	Intermediate Similarity	NPD4221	Approved
0.764	Intermediate Similarity	NPD4753	Phase 2
0.7629	Intermediate Similarity	NPD5739	Approved
0.7629	Intermediate Similarity	NPD7128	Approved
0.7629	Intermediate Similarity	NPD6675	Approved
0.7629	Intermediate Similarity	NPD6402	Approved
0.7619	Intermediate Similarity	NPD7525	Registered
0.7604	Intermediate Similarity	NPD5174	Approved
0.7604	Intermediate Similarity	NPD4754	Approved
0.7604	Intermediate Similarity	NPD5175	Approved
0.759	Intermediate Similarity	NPD6114	Approved
0.759	Intermediate Similarity	NPD6697	Approved
0.759	Intermediate Similarity	NPD6118	Approved
0.759	Intermediate Similarity	NPD6115	Approved
0.7586	Intermediate Similarity	NPD5329	Approved
0.7526	Intermediate Similarity	NPD5141	Approved
0.7475	Intermediate Similarity	NPD6881	Approved
0.7475	Intermediate Similarity	NPD6899	Approved
0.7475	Intermediate Similarity	NPD7320	Approved
0.7473	Intermediate Similarity	NPD7515	Phase 2
0.7471	Intermediate Similarity	NPD4197	Approved
0.7449	Intermediate Similarity	NPD4768	Approved
0.7449	Intermediate Similarity	NPD4767	Approved
0.74	Intermediate Similarity	NPD6373	Approved
0.74	Intermediate Similarity	NPD6372	Approved
0.7381	Intermediate Similarity	NPD3617	Approved
0.7381	Intermediate Similarity	NPD3671	Phase 1
0.7374	Intermediate Similarity	NPD5701	Approved
0.7374	Intermediate Similarity	NPD5697	Approved
0.7349	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD7102	Approved
0.7327	Intermediate Similarity	NPD7290	Approved
0.7327	Intermediate Similarity	NPD6883	Approved
0.7317	Intermediate Similarity	NPD6924	Approved
0.7317	Intermediate Similarity	NPD6926	Approved
0.7303	Intermediate Similarity	NPD4693	Phase 3
0.7303	Intermediate Similarity	NPD4138	Approved
0.7303	Intermediate Similarity	NPD4689	Approved
0.7303	Intermediate Similarity	NPD5205	Approved
0.7303	Intermediate Similarity	NPD5330	Approved
0.7303	Intermediate Similarity	NPD7521	Approved
0.7303	Intermediate Similarity	NPD7334	Approved
0.7303	Intermediate Similarity	NPD4688	Approved
0.7303	Intermediate Similarity	NPD4690	Approved
0.7303	Intermediate Similarity	NPD6409	Approved
0.7303	Intermediate Similarity	NPD6684	Approved
0.7303	Intermediate Similarity	NPD7146	Approved
0.73	Intermediate Similarity	NPD6011	Approved
0.73	Intermediate Similarity	NPD5168	Approved
0.73	Intermediate Similarity	NPD5128	Approved
0.73	Intermediate Similarity	NPD4730	Approved
0.73	Intermediate Similarity	NPD4729	Approved
0.7284	Intermediate Similarity	NPD4758	Discontinued
0.7263	Intermediate Similarity	NPD6083	Phase 2
0.7263	Intermediate Similarity	NPD6084	Phase 2
0.7255	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6650	Approved
0.7255	Intermediate Similarity	NPD8130	Phase 1
0.7255	Intermediate Similarity	NPD6617	Approved
0.7255	Intermediate Similarity	NPD6869	Approved
0.7255	Intermediate Similarity	NPD6649	Approved
0.7255	Intermediate Similarity	NPD6847	Approved
0.7234	Intermediate Similarity	NPD5210	Approved
0.7234	Intermediate Similarity	NPD4629	Approved
0.7228	Intermediate Similarity	NPD6014	Approved
0.7228	Intermediate Similarity	NPD6012	Approved
0.7228	Intermediate Similarity	NPD6013	Approved
0.7184	Intermediate Similarity	NPD8297	Approved
0.7184	Intermediate Similarity	NPD6882	Approved
0.7157	Intermediate Similarity	NPD5135	Approved
0.7157	Intermediate Similarity	NPD5249	Phase 3
0.7157	Intermediate Similarity	NPD5169	Approved
0.7157	Intermediate Similarity	NPD5251	Approved
0.7157	Intermediate Similarity	NPD5250	Approved
0.7157	Intermediate Similarity	NPD4634	Approved
0.7157	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5248	Approved
0.7157	Intermediate Similarity	NPD5247	Approved
0.7143	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD6672	Approved
0.7143	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD6933	Approved
0.7143	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7748	Approved
0.7126	Intermediate Similarity	NPD4692	Approved
0.7126	Intermediate Similarity	NPD4139	Approved
0.7111	Intermediate Similarity	NPD4694	Approved
0.7111	Intermediate Similarity	NPD5280	Approved
0.7111	Intermediate Similarity	NPD5690	Phase 2
0.7111	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4224	Phase 2
0.7087	Intermediate Similarity	NPD5215	Approved
0.7087	Intermediate Similarity	NPD5216	Approved
0.7087	Intermediate Similarity	NPD5217	Approved
0.7087	Intermediate Similarity	NPD5127	Approved
0.7073	Intermediate Similarity	NPD7151	Approved
0.7073	Intermediate Similarity	NPD7152	Approved
0.7073	Intermediate Similarity	NPD7150	Approved
0.7073	Intermediate Similarity	NPD6081	Approved
0.7037	Intermediate Similarity	NPD6923	Approved
0.7037	Intermediate Similarity	NPD6922	Approved
0.7024	Intermediate Similarity	NPD3702	Approved
0.701	Intermediate Similarity	NPD7638	Approved
0.6981	Remote Similarity	NPD6868	Approved
0.6977	Remote Similarity	NPD5364	Discontinued
0.6977	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD4632	Approved
0.6951	Remote Similarity	NPD4747	Approved
0.6951	Remote Similarity	NPD7144	Approved
0.6951	Remote Similarity	NPD7143	Approved
0.6939	Remote Similarity	NPD7640	Approved
0.6939	Remote Similarity	NPD7639	Approved
0.6923	Remote Similarity	NPD6098	Approved
0.6907	Remote Similarity	NPD7902	Approved
0.6897	Remote Similarity	NPD6929	Approved
0.6897	Remote Similarity	NPD7645	Phase 2
0.6897	Remote Similarity	NPD4195	Approved
0.6887	Remote Similarity	NPD5167	Approved
0.6875	Remote Similarity	NPD5695	Phase 3
0.6867	Remote Similarity	NPD5777	Approved
0.6867	Remote Similarity	NPD4243	Approved
0.6852	Remote Similarity	NPD6335	Approved
0.6837	Remote Similarity	NPD5696	Approved
0.6829	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4137	Phase 3
0.6822	Remote Similarity	NPD6274	Approved
0.6818	Remote Similarity	NPD4748	Discontinued
0.6818	Remote Similarity	NPD7509	Discontinued
0.6818	Remote Similarity	NPD5368	Approved
0.6818	Remote Similarity	NPD4695	Discontinued
0.6818	Remote Similarity	NPD6930	Phase 2
0.6818	Remote Similarity	NPD6931	Approved
0.6789	Remote Similarity	NPD7100	Approved
0.6789	Remote Similarity	NPD7101	Approved
0.6765	Remote Similarity	NPD6008	Approved
0.6759	Remote Similarity	NPD6317	Approved
0.6759	Remote Similarity	NPD6009	Approved
0.6747	Remote Similarity	NPD4691	Approved
0.6747	Remote Similarity	NPD4787	Phase 1
0.6739	Remote Similarity	NPD4623	Approved
0.6739	Remote Similarity	NPD4519	Discontinued
0.6737	Remote Similarity	NPD6411	Approved
0.6737	Remote Similarity	NPD5281	Approved
0.6737	Remote Similarity	NPD5284	Approved
0.6727	Remote Similarity	NPD6054	Approved
0.6727	Remote Similarity	NPD6059	Approved
0.6707	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4784	Approved
0.6706	Remote Similarity	NPD4785	Approved
0.6706	Remote Similarity	NPD5733	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