NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.15
Volume:	269.395
LogP:	-0.023
LogD:	-0.522
LogS:	-1.335
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.635
Synthetic Accessibility Score:	4.493
Fsp3:	0.643
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.386
MDCK Permeability:	0.0012239617062732577
Pgp-inhibitor:	0.0
Pgp-substrate:	0.043
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.055
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.63
Plasma Protein Binding (PPB):	31.824485778808594%
Volume Distribution (VD):	0.425
Pgp-substrate:	46.1025276184082%

ADMET: Metabolism

CYP1A2-inhibitor:	0.044
CYP1A2-substrate:	0.249
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.461
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.957
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.012
CYP3A4-substrate:	0.104

ADMET: Excretion

Clearance (CL):	3.13
Half-life (T1/2):	0.796

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.218
Drug-inuced Liver Injury (DILI):	0.273
AMES Toxicity:	0.086
Rat Oral Acute Toxicity:	0.192
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.111
Carcinogencity:	0.283
Eye Corrosion:	0.004
Eye Irritation:	0.137
Respiratory Toxicity:	0.237

Download Data

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

Natural Product: NPC136114

Natural Product ID:	NPC136114
*Common Name:**	(2R,3S,5R,6R)-3-((1E,3E)-Hepta-1,3-Dienyl)-5,6-Dihydroxy-2-Hydroxymethyl-Cyclohexanone
IUPAC Name:	(2R,3R,5S,6R)-5-[(1E,3E)-hepta-1,3-dienyl]-2,3-dihydroxy-6-(hydroxymethyl)cyclohexan-1-one
Synonyms:	NSC-246119
Standard InCHIKey:	MPOXQBRZHHNMER-XZQMCIKJSA-N
Standard InCHI:	InChI=1S/C14H22O4/c1-2-3-4-5-6-7-10-8-12(16)14(18)13(17)11(10)9-15/h4-7,10-12,14-16,18H,2-3,8-9H2,1H3/b5-4+,7-6+/t10-,11+,12-,14-/m1/s1
SMILES:	CCC/C=C/C=C/[C@@H]1C[C@H]([C@H](C(=O)[C@H]1CO)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL367001
PubChem CID:	6438427
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic 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
NPO21233	Pteris linearis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10938	Psychotria prunifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15947	Penicillium glabrum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21233	Pteris linearis	Species	Pteridaceae	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	8
Others	2

Activity Type	# Activity
Individual Protein	10

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	Inhibition	=	57.9	%	PMID[545775]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	Inhibition	=	65.6	%	PMID[545775]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	350000.0	nM	PMID[545775]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	289000.0	nM	PMID[545775]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	268000.0	nM	PMID[545775]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	135000.0	nM	PMID[545775]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	89.0	ug.mL-1	PMID[545775]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	74.0	ug.mL-1	PMID[545775]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	68.0	ug.mL-1	PMID[545775]
NPT12	Individual Protein	Human immunodeficiency virus type 1 integrase	Human immunodeficiency virus 1	IC50	=	34.0	ug.mL-1	PMID[545775]

☑ 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 NPC136114 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	177
0.1-0.2	1146
0.2-0.3	4621
0.3-0.4	9506
0.4-0.5	16272
0.5-0.6	8466
0.6-0.7	2447
0.7-0.8	58
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.8718	High Similarity	NPC476649
0.8372	Intermediate Similarity	NPC262026
0.7667	Intermediate Similarity	NPC298904
0.7667	Intermediate Similarity	NPC472324
0.764	Intermediate Similarity	NPC79573
0.7586	Intermediate Similarity	NPC67254
0.7556	Intermediate Similarity	NPC475753
0.7553	Intermediate Similarity	NPC478089
0.75	Intermediate Similarity	NPC256902
0.75	Intermediate Similarity	NPC118193
0.75	Intermediate Similarity	NPC236176
0.7475	Intermediate Similarity	NPC320294
0.7419	Intermediate Similarity	NPC472325
0.74	Intermediate Similarity	NPC160843
0.7396	Intermediate Similarity	NPC279722
0.7391	Intermediate Similarity	NPC158778
0.7368	Intermediate Similarity	NPC196227
0.7327	Intermediate Similarity	NPC166607
0.732	Intermediate Similarity	NPC273269
0.7312	Intermediate Similarity	NPC473100
0.73	Intermediate Similarity	NPC117185
0.7292	Intermediate Similarity	NPC272617
0.7292	Intermediate Similarity	NPC280725
0.7284	Intermediate Similarity	NPC476650
0.7234	Intermediate Similarity	NPC473099
0.7228	Intermediate Similarity	NPC284865
0.7222	Intermediate Similarity	NPC312480
0.7216	Intermediate Similarity	NPC11396
0.7216	Intermediate Similarity	NPC21302
0.7212	Intermediate Similarity	NPC210005
0.7212	Intermediate Similarity	NPC235077
0.7204	Intermediate Similarity	NPC201046
0.72	Intermediate Similarity	NPC478176
0.7191	Intermediate Similarity	NPC14151
0.7188	Intermediate Similarity	NPC298919
0.7158	Intermediate Similarity	NPC230623
0.7158	Intermediate Similarity	NPC116726
0.7143	Intermediate Similarity	NPC471916
0.7143	Intermediate Similarity	NPC134454
0.7143	Intermediate Similarity	NPC171888
0.7143	Intermediate Similarity	NPC17326
0.7143	Intermediate Similarity	NPC146945
0.7143	Intermediate Similarity	NPC473161
0.7129	Intermediate Similarity	NPC191892
0.7128	Intermediate Similarity	NPC97577
0.7113	Intermediate Similarity	NPC41070
0.7113	Intermediate Similarity	NPC248574
0.7111	Intermediate Similarity	NPC48362
0.71	Intermediate Similarity	NPC470184
0.7093	Intermediate Similarity	NPC114236
0.7087	Intermediate Similarity	NPC144854
0.7087	Intermediate Similarity	NPC3316
0.7083	Intermediate Similarity	NPC478036
0.7083	Intermediate Similarity	NPC478037
0.7079	Intermediate Similarity	NPC157895
0.7079	Intermediate Similarity	NPC104120
0.7079	Intermediate Similarity	NPC148685
0.7071	Intermediate Similarity	NPC191565
0.7071	Intermediate Similarity	NPC469565
0.7065	Intermediate Similarity	NPC15807
0.7065	Intermediate Similarity	NPC36350
0.7065	Intermediate Similarity	NPC187529
0.7059	Intermediate Similarity	NPC326024
0.7059	Intermediate Similarity	NPC475036
0.7045	Intermediate Similarity	NPC178852
0.7041	Intermediate Similarity	NPC469369
0.7041	Intermediate Similarity	NPC469528
0.7041	Intermediate Similarity	NPC94337
0.7033	Intermediate Similarity	NPC64600
0.7033	Intermediate Similarity	NPC105173
0.7019	Intermediate Similarity	NPC293850
0.7019	Intermediate Similarity	NPC154608
0.7019	Intermediate Similarity	NPC192813
0.7019	Intermediate Similarity	NPC277017
0.7011	Intermediate Similarity	NPC78935
0.701	Intermediate Similarity	NPC103527
0.701	Intermediate Similarity	NPC473172
0.701	Intermediate Similarity	NPC470957
0.701	Intermediate Similarity	NPC470958
0.701	Intermediate Similarity	NPC258674
0.7009	Intermediate Similarity	NPC7921
0.7009	Intermediate Similarity	NPC477266
0.7009	Intermediate Similarity	NPC208998
0.7009	Intermediate Similarity	NPC198539
0.7	Intermediate Similarity	NPC46761
0.7	Intermediate Similarity	NPC15390
0.7	Intermediate Similarity	NPC110149
0.699	Remote Similarity	NPC32006
0.699	Remote Similarity	NPC85529
0.6989	Remote Similarity	NPC179591
0.6989	Remote Similarity	NPC202394
0.6979	Remote Similarity	NPC168027
0.6979	Remote Similarity	NPC99380
0.6979	Remote Similarity	NPC36491
0.6979	Remote Similarity	NPC19114
0.6979	Remote Similarity	NPC142838
0.6979	Remote Similarity	NPC185936
0.6979	Remote Similarity	NPC473167
0.697	Remote Similarity	NPC472073
0.697	Remote Similarity	NPC472074
0.697	Remote Similarity	NPC170978
0.6952	Remote Similarity	NPC141350
0.6947	Remote Similarity	NPC69627
0.6944	Remote Similarity	NPC247069
0.6939	Remote Similarity	NPC127063
0.6939	Remote Similarity	NPC322188
0.6939	Remote Similarity	NPC88310
0.6939	Remote Similarity	NPC476245
0.6932	Remote Similarity	NPC197659
0.6931	Remote Similarity	NPC207885
0.6931	Remote Similarity	NPC112613
0.6923	Remote Similarity	NPC212083
0.6923	Remote Similarity	NPC43285
0.6923	Remote Similarity	NPC165873
0.6923	Remote Similarity	NPC58370
0.6916	Remote Similarity	NPC205534
0.6915	Remote Similarity	NPC141292
0.6915	Remote Similarity	NPC86005
0.6915	Remote Similarity	NPC477926
0.6907	Remote Similarity	NPC61275
0.69	Remote Similarity	NPC177232
0.69	Remote Similarity	NPC212465
0.6893	Remote Similarity	NPC477812
0.6893	Remote Similarity	NPC29705
0.6889	Remote Similarity	NPC471266
0.6889	Remote Similarity	NPC470947
0.6889	Remote Similarity	NPC103634
0.6889	Remote Similarity	NPC470945
0.6889	Remote Similarity	NPC472948
0.6889	Remote Similarity	NPC95124
0.6889	Remote Similarity	NPC470946
0.6882	Remote Similarity	NPC471267
0.6881	Remote Similarity	NPC207217
0.6875	Remote Similarity	NPC128672
0.6875	Remote Similarity	NPC313670
0.6875	Remote Similarity	NPC129913
0.6875	Remote Similarity	NPC136801
0.6875	Remote Similarity	NPC316228
0.6875	Remote Similarity	NPC469464
0.6875	Remote Similarity	NPC134321
0.6869	Remote Similarity	NPC307282
0.6869	Remote Similarity	NPC473164
0.6869	Remote Similarity	NPC471153
0.6869	Remote Similarity	NPC473291
0.6869	Remote Similarity	NPC49371
0.6869	Remote Similarity	NPC201657
0.6869	Remote Similarity	NPC19376
0.6869	Remote Similarity	NPC305464
0.6869	Remote Similarity	NPC25848
0.6869	Remote Similarity	NPC473158
0.6863	Remote Similarity	NPC474747
0.6863	Remote Similarity	NPC478156
0.6857	Remote Similarity	NPC168883
0.6857	Remote Similarity	NPC208461
0.6857	Remote Similarity	NPC289702
0.6854	Remote Similarity	NPC478084
0.6852	Remote Similarity	NPC321496
0.6852	Remote Similarity	NPC326264
0.6848	Remote Similarity	NPC477784
0.6848	Remote Similarity	NPC471987
0.6848	Remote Similarity	NPC477786
0.6848	Remote Similarity	NPC278648
0.6848	Remote Similarity	NPC476082
0.6848	Remote Similarity	NPC477785
0.6847	Remote Similarity	NPC323532
0.6847	Remote Similarity	NPC469488
0.6842	Remote Similarity	NPC292491
0.6842	Remote Similarity	NPC87189
0.6842	Remote Similarity	NPC476706
0.6842	Remote Similarity	NPC476707
0.6842	Remote Similarity	NPC310752
0.6842	Remote Similarity	NPC228415
0.6837	Remote Similarity	NPC245972
0.6837	Remote Similarity	NPC196485
0.6837	Remote Similarity	NPC293086
0.6837	Remote Similarity	NPC473162
0.6837	Remote Similarity	NPC209662
0.6837	Remote Similarity	NPC471207
0.6837	Remote Similarity	NPC472976
0.6837	Remote Similarity	NPC474529
0.6837	Remote Similarity	NPC472977
0.6832	Remote Similarity	NPC472972
0.6832	Remote Similarity	NPC127408
0.6832	Remote Similarity	NPC291785
0.6832	Remote Similarity	NPC144956
0.6832	Remote Similarity	NPC306856
0.6832	Remote Similarity	NPC470388
0.6827	Remote Similarity	NPC97202
0.6827	Remote Similarity	NPC302607
0.6827	Remote Similarity	NPC202167
0.6827	Remote Similarity	NPC260268
0.6827	Remote Similarity	NPC150531
0.6827	Remote Similarity	NPC50692
0.6827	Remote Similarity	NPC102352
0.6827	Remote Similarity	NPC85829
0.6827	Remote Similarity	NPC214264
0.6827	Remote Similarity	NPC319077
0.6827	Remote Similarity	NPC48733
0.6827	Remote Similarity	NPC49958
0.6827	Remote Similarity	NPC171137

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 NPC136114 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1594
0.2-0.3	3880
0.3-0.4	2355
0.4-0.5	764
0.5-0.6	307
0.6-0.7	86
0.7-0.8	2
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
0.7263	Intermediate Similarity	NPD5779	Approved
0.7263	Intermediate Similarity	NPD5778	Approved
0.7212	Intermediate Similarity	NPD4634	Approved
0.7128	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6101	Approved
0.6979	Remote Similarity	NPD6411	Approved
0.6979	Remote Similarity	NPD7983	Approved
0.6869	Remote Similarity	NPD5221	Approved
0.6869	Remote Similarity	NPD5222	Approved
0.6869	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4696	Approved
0.6832	Remote Similarity	NPD5286	Approved
0.6832	Remote Similarity	NPD5285	Approved
0.6809	Remote Similarity	NPD5279	Phase 3
0.68	Remote Similarity	NPD5173	Approved
0.68	Remote Similarity	NPD4755	Approved
0.6765	Remote Similarity	NPD5223	Approved
0.6703	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5368	Approved
0.67	Remote Similarity	NPD4697	Phase 3
0.6699	Remote Similarity	NPD5225	Approved
0.6699	Remote Similarity	NPD5211	Phase 2
0.6699	Remote Similarity	NPD5226	Approved
0.6699	Remote Similarity	NPD4633	Approved
0.6699	Remote Similarity	NPD5224	Approved
0.6697	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD4700	Approved
0.6637	Remote Similarity	NPD6319	Approved
0.6635	Remote Similarity	NPD5174	Approved
0.6635	Remote Similarity	NPD5175	Approved
0.6633	Remote Similarity	NPD6079	Approved
0.6598	Remote Similarity	NPD5328	Approved
0.6571	Remote Similarity	NPD5141	Approved
0.6559	Remote Similarity	NPD3667	Approved
0.6559	Remote Similarity	NPD6435	Approved
0.6506	Remote Similarity	NPD3197	Phase 1
0.6491	Remote Similarity	NPD6054	Approved
0.6489	Remote Similarity	NPD6110	Phase 1
0.6476	Remote Similarity	NPD4754	Approved
0.6458	Remote Similarity	NPD3618	Phase 1
0.6458	Remote Similarity	NPD5786	Approved
0.6452	Remote Similarity	NPD5369	Approved
0.6449	Remote Similarity	NPD5697	Approved
0.6435	Remote Similarity	NPD6015	Approved
0.6435	Remote Similarity	NPD6016	Approved
0.6421	Remote Similarity	NPD4786	Approved
0.6389	Remote Similarity	NPD6899	Approved
0.6389	Remote Similarity	NPD4729	Approved
0.6389	Remote Similarity	NPD6011	Approved
0.6389	Remote Similarity	NPD4730	Approved
0.6389	Remote Similarity	NPD6881	Approved
0.6383	Remote Similarity	NPD4270	Approved
0.6383	Remote Similarity	NPD4269	Approved
0.6379	Remote Similarity	NPD5988	Approved
0.6379	Remote Similarity	NPD6370	Approved
0.6373	Remote Similarity	NPD7839	Suspended
0.6372	Remote Similarity	NPD6009	Approved
0.6355	Remote Similarity	NPD4768	Approved
0.6355	Remote Similarity	NPD7128	Approved
0.6355	Remote Similarity	NPD6675	Approved
0.6355	Remote Similarity	NPD4767	Approved
0.6355	Remote Similarity	NPD6402	Approved
0.6355	Remote Similarity	NPD5739	Approved
0.6348	Remote Similarity	NPD6059	Approved
0.6344	Remote Similarity	NPD4695	Discontinued
0.6344	Remote Similarity	NPD4252	Approved
0.633	Remote Similarity	NPD6012	Approved
0.633	Remote Similarity	NPD6014	Approved
0.633	Remote Similarity	NPD6013	Approved
0.6325	Remote Similarity	NPD8328	Phase 3
0.6306	Remote Similarity	NPD8297	Approved
0.63	Remote Similarity	NPD7515	Phase 2
0.6296	Remote Similarity	NPD5701	Approved
0.6275	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5250	Approved
0.6273	Remote Similarity	NPD5169	Approved
0.6273	Remote Similarity	NPD5247	Approved
0.6273	Remote Similarity	NPD5251	Approved
0.6273	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5249	Phase 3
0.6273	Remote Similarity	NPD7102	Approved
0.6273	Remote Similarity	NPD7290	Approved
0.6273	Remote Similarity	NPD5135	Approved
0.6273	Remote Similarity	NPD5248	Approved
0.6273	Remote Similarity	NPD6883	Approved
0.6271	Remote Similarity	NPD7492	Approved
0.6263	Remote Similarity	NPD4753	Phase 2
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD3133	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.6239	Remote Similarity	NPD5128	Approved
0.6239	Remote Similarity	NPD5168	Approved
0.6239	Remote Similarity	NPD7320	Approved
0.6238	Remote Similarity	NPD4202	Approved
0.6218	Remote Similarity	NPD6616	Approved
0.6216	Remote Similarity	NPD6847	Approved
0.6216	Remote Similarity	NPD6617	Approved
0.6216	Remote Similarity	NPD6649	Approved
0.6216	Remote Similarity	NPD6869	Approved
0.6216	Remote Similarity	NPD6650	Approved
0.6216	Remote Similarity	NPD5215	Approved
0.6216	Remote Similarity	NPD8130	Phase 1
0.6216	Remote Similarity	NPD5216	Approved
0.6216	Remote Similarity	NPD5217	Approved
0.6216	Remote Similarity	NPD5127	Approved
0.6211	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD5363	Approved
0.6186	Remote Similarity	NPD1696	Phase 3
0.6182	Remote Similarity	NPD6372	Approved
0.6182	Remote Similarity	NPD6373	Approved
0.6167	Remote Similarity	NPD7078	Approved
0.6163	Remote Similarity	NPD7331	Phase 2
0.6161	Remote Similarity	NPD6882	Approved
0.6154	Remote Similarity	NPD6921	Approved
0.6154	Remote Similarity	NPD5983	Phase 2
0.6139	Remote Similarity	NPD7637	Suspended
0.6129	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD4694	Approved
0.6122	Remote Similarity	NPD5280	Approved
0.6121	Remote Similarity	NPD4522	Approved
0.6117	Remote Similarity	NPD5210	Approved
0.6117	Remote Similarity	NPD4629	Approved
0.6116	Remote Similarity	NPD7736	Approved
0.6092	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD6933	Approved
0.6082	Remote Similarity	NPD3668	Phase 3
0.6078	Remote Similarity	NPD6399	Phase 3
0.6071	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7524	Approved
0.6053	Remote Similarity	NPD5167	Approved
0.605	Remote Similarity	NPD7604	Phase 2
0.6047	Remote Similarity	NPD7341	Phase 2
0.604	Remote Similarity	NPD46	Approved
0.604	Remote Similarity	NPD6698	Approved
0.6033	Remote Similarity	NPD8293	Discontinued
0.6019	Remote Similarity	NPD7748	Approved
0.6017	Remote Similarity	NPD8517	Approved
0.6017	Remote Similarity	NPD8515	Approved
0.6017	Remote Similarity	NPD8516	Approved
0.6017	Remote Similarity	NPD8513	Phase 3
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD7902	Approved
0.5984	Remote Similarity	NPD6033	Approved
0.5981	Remote Similarity	NPD5344	Discontinued
0.598	Remote Similarity	NPD5281	Approved
0.598	Remote Similarity	NPD5284	Approved
0.5978	Remote Similarity	NPD3703	Phase 2
0.596	Remote Similarity	NPD5690	Phase 2
0.596	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD4271	Approved
0.5957	Remote Similarity	NPD4268	Approved
0.595	Remote Similarity	NPD6336	Discontinued
0.5948	Remote Similarity	NPD6317	Approved
0.5943	Remote Similarity	NPD4225	Approved
0.5941	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4197	Approved
0.5897	Remote Similarity	NPD6313	Approved
0.5897	Remote Similarity	NPD6335	Approved
0.5897	Remote Similarity	NPD6314	Approved
0.5895	Remote Similarity	NPD6929	Approved
0.5893	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6648	Approved
0.5882	Remote Similarity	NPD7838	Discovery
0.5882	Remote Similarity	NPD5785	Approved
0.587	Remote Similarity	NPD6926	Approved
0.587	Remote Similarity	NPD6924	Approved
0.5862	Remote Similarity	NPD6868	Approved
0.5862	Remote Similarity	NPD6274	Approved
0.5859	Remote Similarity	NPD5329	Approved
0.5856	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD6932	Approved
0.5849	Remote Similarity	NPD6084	Phase 2
0.5849	Remote Similarity	NPD6083	Phase 2
0.5847	Remote Similarity	NPD7100	Approved
0.5847	Remote Similarity	NPD7101	Approved
0.5833	Remote Similarity	NPD4822	Approved
0.5833	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD4819	Approved
0.5833	Remote Similarity	NPD7509	Discontinued
0.5833	Remote Similarity	NPD6931	Approved
0.5833	Remote Similarity	NPD7525	Registered
0.5833	Remote Similarity	NPD6930	Phase 2
0.5833	Remote Similarity	NPD4820	Approved
0.5833	Remote Similarity	NPD4821	Approved
0.5827	Remote Similarity	NPD8415	Approved
0.5825	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD7151	Approved
0.5824	Remote Similarity	NPD7152	Approved
0.5824	Remote Similarity	NPD7150	Approved
0.5816	Remote Similarity	NPD5362	Discontinued
0.5816	Remote Similarity	NPD6695	Phase 3
0.5814	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5812	Remote Similarity	NPD7115	Discovery
0.581	Remote Similarity	NPD5695	Phase 3
0.5806	Remote Similarity	NPD8264	Approved
0.5804	Remote Similarity	NPD6686	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