NPASS Compound

Structure

NPC471468 OpenBabel07101719252D 29 32 0 0 1 0 0 0 0 0999 V2000 -5.7633 -5.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1161 -6.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 -2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 -2.4135 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 1.7321 -0.0000 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 -3.4980 -4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 -3.5032 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 -4.1369 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 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 0.8660 -0.5000 0.0000 C 0 0 0 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 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7852 -5.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4762 -4.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 -2.7601 0.0000 C 0 0 2 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 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 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 1 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 0.0000 -0.0000 0.0000 C 0 0 1 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 19 1 0 0 0 0 2 19 1 0 0 0 0 3 20 2 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 16 1 0 0 0 0 8 22 2 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 22 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 26 1 0 0 0 0 16 28 1 0 0 0 0 17 27 1 0 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 21 4 1 1 0 0 0 21 24 1 0 0 0 0 22 28 1 0 0 0 0 23 12 1 6 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 27 1 1 0 0 0 25 27 1 1 0 0 0 26 28 1 1 0 0 0 27 5 1 1 0 0 0 28 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.32
Volume:	456.863
LogP:	7.041
LogD:	5.875
LogS:	-6.001
# Rotatable Bonds:	6
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.476
Synthetic Accessibility Score:	4.865
Fsp3:	0.714
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:	-4.717
MDCK Permeability:	3.1886494980426505e-05
Pgp-inhibitor:	0.968
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.213
Plasma Protein Binding (PPB):	98.0364990234375%
Volume Distribution (VD):	1.562
Pgp-substrate:	2.419299364089966%

ADMET: Metabolism

CYP1A2-inhibitor:	0.492
CYP1A2-substrate:	0.292
CYP2C19-inhibitor:	0.222
CYP2C19-substrate:	0.937
CYP2C9-inhibitor:	0.365
CYP2C9-substrate:	0.174
CYP2D6-inhibitor:	0.714
CYP2D6-substrate:	0.867
CYP3A4-inhibitor:	0.943
CYP3A4-substrate:	0.794

ADMET: Excretion

Clearance (CL):	6.563
Half-life (T1/2):	0.057

ADMET: Toxicity

hERG Blockers:	0.955
Human Hepatotoxicity (H-HT):	0.388
Drug-inuced Liver Injury (DILI):	0.133
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.403
Maximum Recommended Daily Dose:	0.583
Skin Sensitization:	0.969
Carcinogencity:	0.415
Eye Corrosion:	0.054
Eye Irritation:	0.057
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC471468

Natural Product ID:	NPC471468
*Common Name:**	24-Methylenecholesta-2,4,6-Trien-19-Ol
IUPAC Name:	[(8S,9S,10S,13R,14S,17R)-13-methyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-8,9,11,12,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-10-yl]methanol
Synonyms:
Standard InCHIKey:	ULVOHMDXTRQASQ-ZDAAFACHSA-N
Standard InCHI:	InChI=1S/C28H42O/c1-19(2)20(3)9-10-21(4)24-13-14-25-23-12-11-22-8-6-7-16-28(22,18-29)26(23)15-17-27(24,25)5/h6-8,11-12,19,21,23-26,29H,3,9-10,13-18H2,1-2,4-5H3/t21-,23+,24-,25+,26+,27-,28-/m1/s1
SMILES:	CC(C)C(=C)CCC(C)C1CCC2C1(CCC3C2C=CC4=CC=CCC34CO)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL251693
PubChem CID:	23642714
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
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	formosan soft coral	n.a.	PMID[17845002]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[24370010]
NPO13916	Nephthea erecta	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9722490]
NPO13916	Nephthea erecta	Species	Nephtheidae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	10.0	ug ml-1	PMID[456092]
NPT168	Cell Line	P388	Mus musculus	ED50	>	10.0	ug ml-1	PMID[456092]

☑ 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 NPC471468 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	150
0.1-0.2	1235
0.2-0.3	8212
0.3-0.4	15666
0.4-0.5	8615
0.5-0.6	5729
0.6-0.7	2422
0.7-0.8	537
0.8-0.85	86
0.85-0.9	39
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9315	High Similarity	NPC18603
0.9315	High Similarity	NPC307965
0.9315	High Similarity	NPC76931
0.913	High Similarity	NPC216460
0.9054	High Similarity	NPC205455
0.9054	High Similarity	NPC186191
0.9041	High Similarity	NPC470362
0.9041	High Similarity	NPC113733
0.8961	High Similarity	NPC470384
0.8904	High Similarity	NPC285893
0.8904	High Similarity	NPC134847
0.8904	High Similarity	NPC162742
0.8904	High Similarity	NPC28657
0.8904	High Similarity	NPC136188
0.8904	High Similarity	NPC22105
0.8904	High Similarity	NPC304309
0.8904	High Similarity	NPC230301
0.8904	High Similarity	NPC288035
0.8857	High Similarity	NPC160209
0.8857	High Similarity	NPC32055
0.8846	High Similarity	NPC238485
0.8831	High Similarity	NPC201852
0.88	High Similarity	NPC318136
0.88	High Similarity	NPC275910
0.8784	High Similarity	NPC46160
0.8784	High Similarity	NPC321016
0.8784	High Similarity	NPC134330
0.8784	High Similarity	NPC107059
0.8784	High Similarity	NPC300324
0.8784	High Similarity	NPC321381
0.8784	High Similarity	NPC240604
0.8784	High Similarity	NPC129165
0.8784	High Similarity	NPC202642
0.8714	High Similarity	NPC197805
0.8696	High Similarity	NPC163678
0.8667	High Similarity	NPC198968
0.8667	High Similarity	NPC318495
0.8667	High Similarity	NPC34019
0.8667	High Similarity	NPC155986
0.8667	High Similarity	NPC214570
0.8649	High Similarity	NPC322353
0.8649	High Similarity	NPC141071
0.8649	High Similarity	NPC118508
0.8649	High Similarity	NPC121744
0.8649	High Similarity	NPC471723
0.8649	High Similarity	NPC257347
0.863	High Similarity	NPC474140
0.8611	High Similarity	NPC475728
0.8611	High Similarity	NPC9161
0.8611	High Similarity	NPC49422
0.8608	High Similarity	NPC231310
0.859	High Similarity	NPC202389
0.8571	High Similarity	NPC286669
0.8571	High Similarity	NPC149680
0.8571	High Similarity	NPC222366
0.8571	High Similarity	NPC234193
0.8571	High Similarity	NPC476039
0.8571	High Similarity	NPC209944
0.8571	High Similarity	NPC164840
0.8571	High Similarity	NPC241290
0.8553	High Similarity	NPC87604
0.8553	High Similarity	NPC473943
0.8553	High Similarity	NPC477522
0.8553	High Similarity	NPC474216
0.8533	High Similarity	NPC247325
0.8533	High Similarity	NPC73875
0.8533	High Similarity	NPC244488
0.8533	High Similarity	NPC189883
0.8514	High Similarity	NPC329090
0.8514	High Similarity	NPC27395
0.8472	Intermediate Similarity	NPC167272
0.8472	Intermediate Similarity	NPC269877
0.8462	Intermediate Similarity	NPC47761
0.8462	Intermediate Similarity	NPC264245
0.8462	Intermediate Similarity	NPC6707
0.8442	Intermediate Similarity	NPC28862
0.8442	Intermediate Similarity	NPC109546
0.8442	Intermediate Similarity	NPC81306
0.8442	Intermediate Similarity	NPC84694
0.8442	Intermediate Similarity	NPC47982
0.8442	Intermediate Similarity	NPC328714
0.8442	Intermediate Similarity	NPC143182
0.84	Intermediate Similarity	NPC319090
0.84	Intermediate Similarity	NPC328104
0.8378	Intermediate Similarity	NPC201373
0.8378	Intermediate Similarity	NPC471799
0.8356	Intermediate Similarity	NPC145498
0.8354	Intermediate Similarity	NPC20853
0.8354	Intermediate Similarity	NPC50964
0.8354	Intermediate Similarity	NPC87489
0.8354	Intermediate Similarity	NPC49964
0.8333	Intermediate Similarity	NPC208999
0.8333	Intermediate Similarity	NPC26117
0.8312	Intermediate Similarity	NPC477514
0.8293	Intermediate Similarity	NPC271967
0.8289	Intermediate Similarity	NPC237460
0.8289	Intermediate Similarity	NPC315261
0.8289	Intermediate Similarity	NPC96319
0.8267	Intermediate Similarity	NPC471797
0.8243	Intermediate Similarity	NPC110799
0.8243	Intermediate Similarity	NPC242001
0.8228	Intermediate Similarity	NPC23852
0.8228	Intermediate Similarity	NPC474531
0.8228	Intermediate Similarity	NPC474683
0.8228	Intermediate Similarity	NPC474752
0.8228	Intermediate Similarity	NPC82986
0.8228	Intermediate Similarity	NPC470383
0.8228	Intermediate Similarity	NPC7505
0.8228	Intermediate Similarity	NPC209620
0.8228	Intermediate Similarity	NPC474731
0.8228	Intermediate Similarity	NPC474759
0.8205	Intermediate Similarity	NPC30986
0.8205	Intermediate Similarity	NPC209430
0.8205	Intermediate Similarity	NPC1319
0.8193	Intermediate Similarity	NPC470542
0.8193	Intermediate Similarity	NPC2158
0.8169	Intermediate Similarity	NPC476737
0.8169	Intermediate Similarity	NPC27243
0.8148	Intermediate Similarity	NPC33913
0.8148	Intermediate Similarity	NPC474493
0.8148	Intermediate Similarity	NPC205845
0.8133	Intermediate Similarity	NPC474743
0.8133	Intermediate Similarity	NPC182717
0.8125	Intermediate Similarity	NPC5985
0.8125	Intermediate Similarity	NPC470614
0.8125	Intermediate Similarity	NPC1272
0.8125	Intermediate Similarity	NPC101462
0.8125	Intermediate Similarity	NPC189972
0.8118	Intermediate Similarity	NPC471453
0.8101	Intermediate Similarity	NPC236112
0.8077	Intermediate Similarity	NPC85346
0.8077	Intermediate Similarity	NPC65897
0.8077	Intermediate Similarity	NPC167037
0.8077	Intermediate Similarity	NPC244385
0.8077	Intermediate Similarity	NPC6978
0.8077	Intermediate Similarity	NPC302041
0.8077	Intermediate Similarity	NPC138621
0.8077	Intermediate Similarity	NPC285761
0.8072	Intermediate Similarity	NPC136548
0.8072	Intermediate Similarity	NPC475772
0.8052	Intermediate Similarity	NPC106432
0.8049	Intermediate Similarity	NPC274448
0.8049	Intermediate Similarity	NPC157257
0.8026	Intermediate Similarity	NPC469593
0.8026	Intermediate Similarity	NPC243342
0.8026	Intermediate Similarity	NPC469533
0.8026	Intermediate Similarity	NPC469534
0.8026	Intermediate Similarity	NPC477138
0.8025	Intermediate Similarity	NPC475789
0.8025	Intermediate Similarity	NPC237795
0.8025	Intermediate Similarity	NPC317458
0.8025	Intermediate Similarity	NPC82538
0.8025	Intermediate Similarity	NPC474634
0.8023	Intermediate Similarity	NPC310013
0.8	Intermediate Similarity	NPC69622
0.8	Intermediate Similarity	NPC107189
0.7975	Intermediate Similarity	NPC80530
0.7975	Intermediate Similarity	NPC273410
0.7952	Intermediate Similarity	NPC222613
0.7952	Intermediate Similarity	NPC475022
0.7952	Intermediate Similarity	NPC89077
0.7952	Intermediate Similarity	NPC261266
0.7952	Intermediate Similarity	NPC118648
0.7949	Intermediate Similarity	NPC91594
0.7949	Intermediate Similarity	NPC471798
0.7927	Intermediate Similarity	NPC185568
0.7927	Intermediate Similarity	NPC209802
0.7927	Intermediate Similarity	NPC124172
0.7927	Intermediate Similarity	NPC472265
0.7927	Intermediate Similarity	NPC59453
0.7927	Intermediate Similarity	NPC221758
0.7927	Intermediate Similarity	NPC470077
0.7927	Intermediate Similarity	NPC473246
0.7922	Intermediate Similarity	NPC291503
0.7901	Intermediate Similarity	NPC248886
0.7901	Intermediate Similarity	NPC470049
0.7901	Intermediate Similarity	NPC30166
0.7901	Intermediate Similarity	NPC218616
0.7901	Intermediate Similarity	NPC296701
0.7895	Intermediate Similarity	NPC130665
0.7895	Intermediate Similarity	NPC68443
0.7882	Intermediate Similarity	NPC77168
0.7882	Intermediate Similarity	NPC102414
0.7882	Intermediate Similarity	NPC84271
0.7875	Intermediate Similarity	NPC102253
0.7875	Intermediate Similarity	NPC322313
0.7875	Intermediate Similarity	NPC324772
0.7875	Intermediate Similarity	NPC13554
0.7875	Intermediate Similarity	NPC22403
0.7875	Intermediate Similarity	NPC236237
0.7867	Intermediate Similarity	NPC34834
0.7857	Intermediate Similarity	NPC58063
0.7857	Intermediate Similarity	NPC149224
0.7848	Intermediate Similarity	NPC167891
0.7848	Intermediate Similarity	NPC72507
0.7848	Intermediate Similarity	NPC83351
0.7848	Intermediate Similarity	NPC312328
0.7831	Intermediate Similarity	NPC474083
0.7831	Intermediate Similarity	NPC474189
0.7831	Intermediate Similarity	NPC318390

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 NPC471468 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1432
0.2-0.3	4407
0.3-0.4	2235
0.4-0.5	530
0.5-0.6	202
0.6-0.7	136
0.7-0.8	40
0.8-0.85	14
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8904	High Similarity	NPD6942	Approved
0.8904	High Similarity	NPD7339	Approved
0.8611	High Similarity	NPD7144	Approved
0.8611	High Similarity	NPD7143	Approved
0.8514	High Similarity	NPD4784	Approved
0.8514	High Similarity	NPD6924	Approved
0.8514	High Similarity	NPD4785	Approved
0.8514	High Similarity	NPD6926	Approved
0.8493	Intermediate Similarity	NPD7152	Approved
0.8493	Intermediate Similarity	NPD7151	Approved
0.8493	Intermediate Similarity	NPD7150	Approved
0.8472	Intermediate Similarity	NPD6923	Approved
0.8472	Intermediate Similarity	NPD6922	Approved
0.8289	Intermediate Similarity	NPD6933	Approved
0.8289	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD4243	Approved
0.7975	Intermediate Similarity	NPD6929	Approved
0.7949	Intermediate Similarity	NPD6932	Approved
0.7927	Intermediate Similarity	NPD4786	Approved
0.7875	Intermediate Similarity	NPD6931	Approved
0.7875	Intermediate Similarity	NPD7525	Registered
0.7875	Intermediate Similarity	NPD6930	Phase 2
0.7848	Intermediate Similarity	NPD7145	Approved
0.7738	Intermediate Similarity	NPD5279	Phase 3
0.7722	Intermediate Similarity	NPD5776	Phase 2
0.7722	Intermediate Similarity	NPD6925	Approved
0.7692	Intermediate Similarity	NPD4190	Phase 3
0.7692	Intermediate Similarity	NPD8264	Approved
0.7692	Intermediate Similarity	NPD5275	Approved
0.7683	Intermediate Similarity	NPD3667	Approved
0.7654	Intermediate Similarity	NPD4748	Discontinued
0.7654	Intermediate Similarity	NPD7509	Discontinued
0.7654	Intermediate Similarity	NPD7514	Phase 3
0.7625	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6695	Phase 3
0.7561	Intermediate Similarity	NPD6902	Approved
0.7531	Intermediate Similarity	NPD6683	Phase 2
0.7531	Intermediate Similarity	NPD4195	Approved
0.75	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD7332	Phase 2
0.7412	Intermediate Similarity	NPD6893	Approved
0.7326	Intermediate Similarity	NPD4694	Approved
0.7326	Intermediate Similarity	NPD5280	Approved
0.7317	Intermediate Similarity	NPD7645	Phase 2
0.7303	Intermediate Similarity	NPD6079	Approved
0.7294	Intermediate Similarity	NPD3666	Approved
0.7294	Intermediate Similarity	NPD3665	Phase 1
0.7294	Intermediate Similarity	NPD3133	Approved
0.7273	Intermediate Similarity	NPD5328	Approved
0.7241	Intermediate Similarity	NPD7524	Approved
0.7241	Intermediate Similarity	NPD7750	Discontinued
0.7143	Intermediate Similarity	NPD6898	Phase 1
0.7126	Intermediate Similarity	NPD5690	Phase 2
0.7126	Intermediate Similarity	NPD3618	Phase 1
0.7111	Intermediate Similarity	NPD5284	Approved
0.7111	Intermediate Similarity	NPD5281	Approved
0.7079	Intermediate Similarity	NPD4753	Phase 2
0.7059	Intermediate Similarity	NPD4221	Approved
0.7059	Intermediate Similarity	NPD4223	Phase 3
0.7033	Intermediate Similarity	NPD6399	Phase 3
0.7011	Intermediate Similarity	NPD5329	Approved
0.6966	Remote Similarity	NPD4518	Approved
0.6923	Remote Similarity	NPD7087	Discontinued
0.6914	Remote Similarity	NPD5733	Approved
0.6914	Remote Similarity	NPD4687	Approved
0.6897	Remote Similarity	NPD3668	Phase 3
0.6897	Remote Similarity	NPD4197	Approved
0.6882	Remote Similarity	NPD5210	Approved
0.6882	Remote Similarity	NPD4629	Approved
0.6848	Remote Similarity	NPD4202	Approved
0.6813	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4096	Approved
0.6809	Remote Similarity	NPD5222	Approved
0.6809	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5221	Approved
0.6806	Remote Similarity	NPD4219	Approved
0.6782	Remote Similarity	NPD4788	Approved
0.6744	Remote Similarity	NPD4139	Approved
0.6744	Remote Similarity	NPD4692	Approved
0.6742	Remote Similarity	NPD4688	Approved
0.6742	Remote Similarity	NPD5205	Approved
0.6742	Remote Similarity	NPD4690	Approved
0.6742	Remote Similarity	NPD4689	Approved
0.6742	Remote Similarity	NPD4693	Phase 3
0.6742	Remote Similarity	NPD4138	Approved
0.6739	Remote Similarity	NPD7637	Suspended
0.6739	Remote Similarity	NPD6411	Approved
0.6737	Remote Similarity	NPD5173	Approved
0.6737	Remote Similarity	NPD6083	Phase 2
0.6737	Remote Similarity	NPD6084	Phase 2
0.6702	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD342	Phase 1
0.6667	Remote Similarity	NPD5276	Approved
0.6667	Remote Similarity	NPD5133	Approved
0.6632	Remote Similarity	NPD4697	Phase 3
0.663	Remote Similarity	NPD5207	Approved
0.663	Remote Similarity	NPD7136	Phase 2
0.6629	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD5285	Approved
0.6598	Remote Similarity	NPD4696	Approved
0.6598	Remote Similarity	NPD5286	Approved
0.6598	Remote Similarity	NPD6404	Discontinued
0.6593	Remote Similarity	NPD6672	Approved
0.6593	Remote Similarity	NPD4722	Approved
0.6593	Remote Similarity	NPD5737	Approved
0.6593	Remote Similarity	NPD4723	Approved
0.6588	Remote Similarity	NPD3617	Approved
0.6562	Remote Similarity	NPD4755	Approved
0.6559	Remote Similarity	NPD5694	Approved
0.6559	Remote Similarity	NPD6050	Approved
0.6556	Remote Similarity	NPD7521	Approved
0.6556	Remote Similarity	NPD7334	Approved
0.6556	Remote Similarity	NPD5330	Approved
0.6556	Remote Similarity	NPD6409	Approved
0.6556	Remote Similarity	NPD7146	Approved
0.6556	Remote Similarity	NPD6684	Approved
0.6531	Remote Similarity	NPD5223	Approved
0.6522	Remote Similarity	NPD6051	Approved
0.6522	Remote Similarity	NPD6101	Approved
0.6522	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4058	Approved
0.6495	Remote Similarity	NPD5290	Discontinued
0.6465	Remote Similarity	NPD4633	Approved
0.6465	Remote Similarity	NPD5225	Approved
0.6465	Remote Similarity	NPD5224	Approved
0.6465	Remote Similarity	NPD5211	Phase 2
0.6465	Remote Similarity	NPD5226	Approved
0.6452	Remote Similarity	NPD5692	Phase 3
0.6437	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD4695	Discontinued
0.6429	Remote Similarity	NPD4700	Approved
0.6413	Remote Similarity	NPD6903	Approved
0.6413	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5174	Approved
0.64	Remote Similarity	NPD5175	Approved
0.6383	Remote Similarity	NPD7515	Phase 2
0.6374	Remote Similarity	NPD6098	Approved
0.6374	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD4623	Approved
0.6374	Remote Similarity	NPD4519	Discontinued
0.6353	Remote Similarity	NPD1346	Approved
0.6341	Remote Similarity	NPD4747	Approved
0.6341	Remote Similarity	NPD6939	Phase 2
0.6341	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5141	Approved
0.6327	Remote Similarity	NPD5696	Approved
0.6327	Remote Similarity	NPD7638	Approved
0.6311	Remote Similarity	NPD6881	Approved
0.6311	Remote Similarity	NPD6899	Approved
0.6296	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD8262	Approved
0.6275	Remote Similarity	NPD6402	Approved
0.6275	Remote Similarity	NPD5739	Approved
0.6275	Remote Similarity	NPD7128	Approved
0.6275	Remote Similarity	NPD6675	Approved
0.6263	Remote Similarity	NPD7639	Approved
0.6263	Remote Similarity	NPD7640	Approved
0.6238	Remote Similarity	NPD4754	Approved
0.622	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.622	Remote Similarity	NPD4137	Phase 3
0.6214	Remote Similarity	NPD5697	Approved
0.6207	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.619	Remote Similarity	NPD6883	Approved
0.619	Remote Similarity	NPD7290	Approved
0.619	Remote Similarity	NPD7102	Approved
0.617	Remote Similarity	NPD6080	Approved
0.617	Remote Similarity	NPD6904	Approved
0.617	Remote Similarity	NPD6673	Approved
0.6154	Remote Similarity	NPD4729	Approved
0.6154	Remote Similarity	NPD5168	Approved
0.6154	Remote Similarity	NPD4730	Approved
0.6154	Remote Similarity	NPD7320	Approved
0.6154	Remote Similarity	NPD368	Approved
0.6154	Remote Similarity	NPD6011	Approved
0.6146	Remote Similarity	NPD5779	Approved
0.6146	Remote Similarity	NPD5778	Approved
0.6145	Remote Similarity	NPD4787	Phase 1
0.6145	Remote Similarity	NPD4789	Approved
0.6145	Remote Similarity	NPD4691	Approved
0.6132	Remote Similarity	NPD6650	Approved
0.6132	Remote Similarity	NPD6617	Approved
0.6132	Remote Similarity	NPD8130	Phase 1
0.6132	Remote Similarity	NPD6847	Approved
0.6132	Remote Similarity	NPD6649	Approved
0.6132	Remote Similarity	NPD6869	Approved
0.6125	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4768	Approved
0.6117	Remote Similarity	NPD4767	Approved
0.6098	Remote Similarity	NPD6705	Phase 1
0.6095	Remote Similarity	NPD6012	Approved
0.6095	Remote Similarity	NPD6372	Approved
0.6095	Remote Similarity	NPD6373	Approved
0.6095	Remote Similarity	NPD6013	Approved
0.6095	Remote Similarity	NPD6014	Approved
0.6087	Remote Similarity	NPD1696	Phase 3
0.6082	Remote Similarity	NPD7748	Approved
0.6082	Remote Similarity	NPD5771	Approved
0.6075	Remote Similarity	NPD8297	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