NPASS Compound

Structure

NPC159367 OpenBabel07101718192D 33 37 0 0 1 0 0 0 0 0999 V2000 -6.7206 2.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0003 -0.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9179 0.6910 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 -8.5747 -3.0020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3604 1.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3386 0.8023 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6665 3.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6720 2.9781 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6257 -0.3567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 -8.9348 -1.3078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2875 -1.8430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0514 1.9612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9785 -0.8920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6476 -0.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0733 2.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 1 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 0.0000 -1.0000 0.0000 C 0 0 2 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 -4.3301 1.5000 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 0.8660 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.2656 -2.0509 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 20 1 0 0 0 0 5 32 1 0 0 0 0 6 7 2 0 0 0 0 6 19 1 0 0 0 0 7 21 1 0 0 0 0 8 9 1 0 0 0 0 8 22 2 0 0 0 0 9 26 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 15 1 0 0 0 0 12 25 1 0 0 0 0 13 16 1 0 0 0 0 13 27 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 32 1 0 0 0 0 18 20 1 0 0 0 0 18 32 1 0 0 0 0 19 1 1 1 0 0 0 19 23 1 0 0 0 0 20 21 2 0 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 29 1 1 0 0 0 24 29 1 1 0 0 0 25 30 1 1 0 0 0 26 28 1 0 0 0 0 26 30 1 1 0 0 0 27 28 1 0 0 0 0 27 31 1 6 0 0 0 28 33 1 6 0 0 0 29 3 1 1 0 0 0 30 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.38
Volume:	507.528
LogP:	4.978
LogD:	5.169
LogS:	-5.527
# Rotatable Bonds:	3
TPSA:	49.49
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.539
Synthetic Accessibility Score:	5.078
Fsp3:	0.8
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:	-5.24
MDCK Permeability:	7.375981113000307e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.109
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.798

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014
Plasma Protein Binding (PPB):	86.80840301513672%
Volume Distribution (VD):	0.795
Pgp-substrate:	2.4365549087524414%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.112
CYP2C19-inhibitor:	0.038
CYP2C19-substrate:	0.945
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.892
CYP2D6-substrate:	0.914
CYP3A4-inhibitor:	0.883
CYP3A4-substrate:	0.87

ADMET: Excretion

Clearance (CL):	3.724
Half-life (T1/2):	0.186

ADMET: Toxicity

hERG Blockers:	0.773
Human Hepatotoxicity (H-HT):	0.79
Drug-inuced Liver Injury (DILI):	0.734
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.295
Maximum Recommended Daily Dose:	0.858
Skin Sensitization:	0.916
Carcinogencity:	0.003
Eye Corrosion:	0.024
Eye Irritation:	0.023
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC159367

Natural Product ID:	NPC159367
*Common Name:**	4Alpha-Hydroxydemethylplakinamine B
IUPAC Name:	(3R,4S,5R,9R,10R,13R,14R,17R)-3-amino-17-[(E,2R)-4-(1,5-dimethyl-3,6-dihydro-2H-pyridin-4-yl)but-3-en-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-4-ol
Synonyms:
Standard InCHIKey:	ZNDZLOQWUMYHMQ-DBXYCEKVSA-N
Standard InCHI:	InChI=1S/C30H48N2O/c1-19(6-7-21-14-17-32(5)18-20(21)2)23-10-11-24-22-8-9-26-28(33)27(31)13-16-30(26,4)25(22)12-15-29(23,24)3/h6-8,19,23-28,33H,9-18,31H2,1-5H3/b7-6+/t19-,23-,24+,25+,26+,27-,28+,29-,30-/m1/s1
SMILES:	CN1CCC(=C(C1)C)/C=C/[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CC[C@H]([C@H]2O)N)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL484040
PubChem CID:	12049602
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO32780	corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193035]
NPO32780	corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17391049]
NPO32780	corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	New Britain, Papua New Guinea	n.a.	PMID[24195491]
NPO32780	corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964780]

☑ 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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT76	Cell Line	C6	Rattus norvegicus	IC50	=	26.1	ug.mL-1	PMID[558314]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	16.2	ug.mL-1	PMID[558314]

☑ 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 NPC159367 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	104
0.1-0.2	850
0.2-0.3	10280
0.3-0.4	16960
0.4-0.5	10071
0.5-0.6	3812
0.6-0.7	570
0.7-0.8	46
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8431	Intermediate Similarity	NPC476903
0.819	Intermediate Similarity	NPC135799
0.8173	Intermediate Similarity	NPC474164
0.8113	Intermediate Similarity	NPC118275
0.7963	Intermediate Similarity	NPC241879
0.7909	Intermediate Similarity	NPC25340
0.787	Intermediate Similarity	NPC471083
0.787	Intermediate Similarity	NPC176012
0.7857	Intermediate Similarity	NPC472313
0.7818	Intermediate Similarity	NPC55462
0.781	Intermediate Similarity	NPC272732
0.781	Intermediate Similarity	NPC311164
0.7736	Intermediate Similarity	NPC289140
0.7719	Intermediate Similarity	NPC474452
0.7636	Intermediate Similarity	NPC474583
0.7632	Intermediate Similarity	NPC474459
0.7596	Intermediate Similarity	NPC84171
0.7593	Intermediate Similarity	NPC91604
0.7565	Intermediate Similarity	NPC56796
0.7545	Intermediate Similarity	NPC50815
0.7545	Intermediate Similarity	NPC58200
0.75	Intermediate Similarity	NPC140300
0.7451	Intermediate Similarity	NPC75810
0.7434	Intermediate Similarity	NPC46981
0.7391	Intermediate Similarity	NPC472359
0.7387	Intermediate Similarity	NPC247060
0.7383	Intermediate Similarity	NPC243985
0.7383	Intermediate Similarity	NPC280710
0.7339	Intermediate Similarity	NPC240650
0.7328	Intermediate Similarity	NPC79238
0.7304	Intermediate Similarity	NPC85001
0.7304	Intermediate Similarity	NPC253645
0.7304	Intermediate Similarity	NPC95920
0.7304	Intermediate Similarity	NPC147835
0.7227	Intermediate Similarity	NPC304646
0.7227	Intermediate Similarity	NPC28280
0.7203	Intermediate Similarity	NPC478137
0.7168	Intermediate Similarity	NPC98765
0.7168	Intermediate Similarity	NPC473254
0.7119	Intermediate Similarity	NPC80834
0.7119	Intermediate Similarity	NPC124358
0.7119	Intermediate Similarity	NPC469968
0.7105	Intermediate Similarity	NPC212874
0.7105	Intermediate Similarity	NPC475239
0.7054	Intermediate Similarity	NPC275686
0.7043	Intermediate Similarity	NPC86906
0.7043	Intermediate Similarity	NPC477292
0.7034	Intermediate Similarity	NPC66862
0.7018	Intermediate Similarity	NPC45365
0.7018	Intermediate Similarity	NPC293299
0.7016	Intermediate Similarity	NPC478138
0.7	Intermediate Similarity	NPC119225
0.7	Intermediate Similarity	NPC476261
0.7	Intermediate Similarity	NPC471635
0.7	Intermediate Similarity	NPC470382
0.7	Intermediate Similarity	NPC25033
0.699	Remote Similarity	NPC472312
0.6984	Remote Similarity	NPC237286
0.6983	Remote Similarity	NPC476756
0.6983	Remote Similarity	NPC244982
0.6972	Remote Similarity	NPC93027
0.6961	Remote Similarity	NPC12035
0.6957	Remote Similarity	NPC470596
0.6949	Remote Similarity	NPC72753
0.6931	Remote Similarity	NPC307965
0.6931	Remote Similarity	NPC205455
0.6931	Remote Similarity	NPC18603
0.6931	Remote Similarity	NPC186191
0.6931	Remote Similarity	NPC76931
0.69	Remote Similarity	NPC189883
0.69	Remote Similarity	NPC129165
0.69	Remote Similarity	NPC134330
0.6897	Remote Similarity	NPC233256
0.6897	Remote Similarity	NPC195841
0.6893	Remote Similarity	NPC329782
0.6893	Remote Similarity	NPC474122
0.6893	Remote Similarity	NPC118329
0.6893	Remote Similarity	NPC152039
0.687	Remote Similarity	NPC90538
0.6863	Remote Similarity	NPC211322
0.6846	Remote Similarity	NPC40488
0.6827	Remote Similarity	NPC20853
0.6822	Remote Similarity	NPC21035
0.68	Remote Similarity	NPC471723
0.68	Remote Similarity	NPC242692
0.68	Remote Similarity	NPC141071
0.68	Remote Similarity	NPC257347
0.6783	Remote Similarity	NPC476755
0.678	Remote Similarity	NPC470595
0.6774	Remote Similarity	NPC35037
0.6765	Remote Similarity	NPC318136
0.6752	Remote Similarity	NPC36497
0.6746	Remote Similarity	NPC472458
0.6733	Remote Similarity	NPC240604
0.6733	Remote Similarity	NPC237460
0.6733	Remote Similarity	NPC470362
0.6733	Remote Similarity	NPC113733
0.6733	Remote Similarity	NPC202642
0.6733	Remote Similarity	NPC300324
0.6733	Remote Similarity	NPC46160
0.6726	Remote Similarity	NPC473537
0.6726	Remote Similarity	NPC167419
0.67	Remote Similarity	NPC476904
0.6699	Remote Similarity	NPC1319
0.6698	Remote Similarity	NPC231310
0.6695	Remote Similarity	NPC169375
0.6667	Remote Similarity	NPC214570
0.6667	Remote Similarity	NPC96010
0.6667	Remote Similarity	NPC475249
0.6667	Remote Similarity	NPC201852
0.6667	Remote Similarity	NPC215474
0.6667	Remote Similarity	NPC202389
0.6667	Remote Similarity	NPC21773
0.6667	Remote Similarity	NPC63511
0.6667	Remote Similarity	NPC317654
0.6667	Remote Similarity	NPC252564
0.6641	Remote Similarity	NPC296686
0.6635	Remote Similarity	NPC236112
0.6634	Remote Similarity	NPC322353
0.6634	Remote Similarity	NPC288035
0.6634	Remote Similarity	NPC22105
0.6634	Remote Similarity	NPC285893
0.6634	Remote Similarity	NPC304309
0.6634	Remote Similarity	NPC118508
0.6634	Remote Similarity	NPC136188
0.6634	Remote Similarity	NPC121744
0.6634	Remote Similarity	NPC230301
0.6634	Remote Similarity	NPC134847
0.6634	Remote Similarity	NPC162742
0.6634	Remote Similarity	NPC28657
0.6634	Remote Similarity	NPC471468
0.6609	Remote Similarity	NPC239768
0.6609	Remote Similarity	NPC128698
0.6609	Remote Similarity	NPC201712
0.6606	Remote Similarity	NPC470542
0.6604	Remote Similarity	NPC470384
0.6604	Remote Similarity	NPC171639
0.6604	Remote Similarity	NPC246956
0.6602	Remote Similarity	NPC6978
0.6602	Remote Similarity	NPC244385
0.6602	Remote Similarity	NPC85346
0.6602	Remote Similarity	NPC275910
0.6602	Remote Similarity	NPC302041
0.6602	Remote Similarity	NPC167037
0.6602	Remote Similarity	NPC285761
0.6602	Remote Similarity	NPC65897
0.6602	Remote Similarity	NPC138621
0.66	Remote Similarity	NPC182717
0.6593	Remote Similarity	NPC132847
0.6579	Remote Similarity	NPC292819
0.6574	Remote Similarity	NPC166458
0.6571	Remote Similarity	NPC474531
0.6571	Remote Similarity	NPC6707
0.6571	Remote Similarity	NPC109533
0.6569	Remote Similarity	NPC247325
0.6569	Remote Similarity	NPC7214
0.6569	Remote Similarity	NPC321381
0.6569	Remote Similarity	NPC321016
0.6569	Remote Similarity	NPC107059
0.6569	Remote Similarity	NPC244488
0.6569	Remote Similarity	NPC106432
0.6569	Remote Similarity	NPC73875
0.6557	Remote Similarity	NPC477291
0.6557	Remote Similarity	NPC476498
0.6552	Remote Similarity	NPC475518
0.6542	Remote Similarity	NPC209802
0.6542	Remote Similarity	NPC474493
0.6542	Remote Similarity	NPC238485
0.6542	Remote Similarity	NPC470077
0.6538	Remote Similarity	NPC209430
0.6538	Remote Similarity	NPC80530
0.6538	Remote Similarity	NPC273410
0.6538	Remote Similarity	NPC30986
0.6535	Remote Similarity	NPC100334
0.6532	Remote Similarity	NPC165396
0.6514	Remote Similarity	NPC43308
0.6509	Remote Similarity	NPC296701
0.6509	Remote Similarity	NPC49964
0.6509	Remote Similarity	NPC30166
0.6509	Remote Similarity	NPC248886
0.6509	Remote Similarity	NPC218616
0.6509	Remote Similarity	NPC470049
0.6509	Remote Similarity	NPC87489
0.6509	Remote Similarity	NPC5985
0.6505	Remote Similarity	NPC198968
0.6505	Remote Similarity	NPC34019
0.6505	Remote Similarity	NPC318495
0.6505	Remote Similarity	NPC155986
0.65	Remote Similarity	NPC265789
0.6496	Remote Similarity	NPC478140
0.6481	Remote Similarity	NPC152684
0.6481	Remote Similarity	NPC318390
0.6481	Remote Similarity	NPC147513
0.6476	Remote Similarity	NPC13554
0.6476	Remote Similarity	NPC102253
0.6476	Remote Similarity	NPC322313
0.6476	Remote Similarity	NPC209944
0.6476	Remote Similarity	NPC241290
0.6476	Remote Similarity	NPC234193
0.6476	Remote Similarity	NPC236237

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 NPC159367 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	97
0.1-0.2	417
0.2-0.3	2582
0.3-0.4	4117
0.4-0.5	1566
0.5-0.6	326
0.6-0.7	45
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6757	Remote Similarity	NPD5771	Approved
0.6726	Remote Similarity	NPD7920	Phase 3
0.6726	Remote Similarity	NPD7919	Phase 3
0.6667	Remote Similarity	NPD8088	Phase 1
0.6634	Remote Similarity	NPD7339	Approved
0.6634	Remote Similarity	NPD6942	Approved
0.6557	Remote Similarity	NPD7335	Phase 2
0.6557	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD7336	Phase 2
0.6532	Remote Similarity	NPD7755	Approved
0.6532	Remote Similarity	NPD7754	Approved
0.6476	Remote Similarity	NPD7525	Registered
0.64	Remote Similarity	NPD7144	Approved
0.64	Remote Similarity	NPD7143	Approved
0.6373	Remote Similarity	NPD6926	Approved
0.6373	Remote Similarity	NPD6924	Approved
0.6337	Remote Similarity	NPD7150	Approved
0.6337	Remote Similarity	NPD7152	Approved
0.6337	Remote Similarity	NPD7151	Approved
0.6333	Remote Similarity	NPD7333	Discontinued
0.63	Remote Similarity	NPD6922	Approved
0.63	Remote Similarity	NPD6923	Approved
0.625	Remote Similarity	NPD8131	Suspended
0.625	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6933	Approved
0.6226	Remote Similarity	NPD7645	Phase 2
0.6214	Remote Similarity	NPD4784	Approved
0.6214	Remote Similarity	NPD4785	Approved
0.6207	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD8449	Approved
0.6176	Remote Similarity	NPD4243	Approved
0.616	Remote Similarity	NPD8077	Approved
0.616	Remote Similarity	NPD8078	Approved
0.614	Remote Similarity	NPD6079	Approved
0.6131	Remote Similarity	NPD8450	Suspended
0.6126	Remote Similarity	NPD8308	Discontinued
0.6106	Remote Similarity	NPD5328	Approved
0.6091	Remote Similarity	NPD4786	Approved
0.6075	Remote Similarity	NPD6929	Approved
0.6066	Remote Similarity	NPD6920	Discontinued
0.6038	Remote Similarity	NPD6932	Approved
0.6031	Remote Similarity	NPD6909	Approved
0.6031	Remote Similarity	NPD6908	Approved
0.6019	Remote Similarity	NPD6931	Approved
0.6019	Remote Similarity	NPD6930	Phase 2
0.6019	Remote Similarity	NPD7509	Discontinued
0.6016	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7522	Discontinued
0.5982	Remote Similarity	NPD3618	Phase 1
0.5981	Remote Similarity	NPD7145	Approved
0.5969	Remote Similarity	NPD4032	Approved
0.5969	Remote Similarity	NPD4031	Approved
0.5968	Remote Similarity	NPD6415	Discontinued
0.5954	Remote Similarity	NPD2227	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD3667	Approved
0.5897	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5776	Phase 2
0.5888	Remote Similarity	NPD6925	Approved
0.5872	Remote Similarity	NPD7514	Phase 3
0.5865	Remote Similarity	NPD5365	Phase 2
0.5856	Remote Similarity	NPD6695	Phase 3
0.5849	Remote Similarity	NPD4190	Phase 3
0.5849	Remote Similarity	NPD5275	Approved
0.5841	Remote Similarity	NPD5279	Phase 3
0.5833	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.582	Remote Similarity	NPD4719	Phase 2
0.5818	Remote Similarity	NPD6902	Approved
0.5812	Remote Similarity	NPD4202	Approved
0.5804	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD3666	Approved
0.5804	Remote Similarity	NPD3133	Approved
0.5804	Remote Similarity	NPD3665	Phase 1
0.5798	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD5222	Approved
0.5798	Remote Similarity	NPD5221	Approved
0.5789	Remote Similarity	NPD1710	Approved
0.5789	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5782	Remote Similarity	NPD3638	Discontinued
0.578	Remote Similarity	NPD6683	Phase 2
0.578	Remote Similarity	NPD4195	Approved
0.5752	Remote Similarity	NPD6893	Approved
0.5752	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.575	Remote Similarity	NPD5173	Approved
0.5739	Remote Similarity	NPD4723	Approved
0.5739	Remote Similarity	NPD4722	Approved
0.5736	Remote Similarity	NPD8298	Phase 2
0.5727	Remote Similarity	NPD4748	Discontinued
0.5727	Remote Similarity	NPD7332	Phase 2
0.5701	Remote Similarity	NPD8264	Approved
0.568	Remote Similarity	NPD5717	Approved
0.5667	Remote Similarity	NPD4697	Phase 3
0.5656	Remote Similarity	NPD5286	Approved
0.5656	Remote Similarity	NPD4696	Approved
0.5656	Remote Similarity	NPD5285	Approved
0.5652	Remote Similarity	NPD7750	Discontinued
0.5652	Remote Similarity	NPD7524	Approved
0.5646	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD7912	Approved
0.5645	Remote Similarity	NPD7986	Approved
0.5645	Remote Similarity	NPD7987	Approved
0.5645	Remote Similarity	NPD7911	Approved
0.563	Remote Similarity	NPD7725	Approved
0.563	Remote Similarity	NPD4416	Clinical (unspecified phase)
0.562	Remote Similarity	NPD4755	Approved
0.561	Remote Similarity	NPD5223	Approved
0.5606	Remote Similarity	NPD7508	Discontinued

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