NPASS Compound

Structure

NPC101012 OpenBabel07101718272D 24 26 0 0 1 0 0 0 0 0999 V2000 -4.8441 -0.1485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5922 1.0484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5145 0.2368 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 -0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4796 -2.0920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8727 0.0886 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 -1.7568 -1.4010 0.0000 C 0 0 0 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 -3.3601 -1.6182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1816 -0.6342 0.0000 C 0 0 1 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 -0.7818 -1.6235 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 -2.1906 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 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 -4.2611 -2.0520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5593 -2.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 19 1 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 13 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 17 2 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 22 1 6 0 0 0 15 16 1 0 0 0 0 15 23 2 0 0 0 0 16 20 1 6 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 24 1 0 0 0 0 19 3 1 1 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	356.058
LogP:	1.892
LogD:	1.009
LogS:	-2.204
# Rotatable Bonds:	2
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.788
Synthetic Accessibility Score:	4.913
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.684
MDCK Permeability:	3.0046949177631177e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.582
Plasma Protein Binding (PPB):	46.67610549926758%
Volume Distribution (VD):	1.849
Pgp-substrate:	52.67121887207031%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.489
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.622
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.14
CYP3A4-inhibitor:	0.164
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	13.834
Half-life (T1/2):	0.341

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.171
Drug-inuced Liver Injury (DILI):	0.609
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.955
Maximum Recommended Daily Dose:	0.041
Skin Sensitization:	0.204
Carcinogencity:	0.059
Eye Corrosion:	0.846
Eye Irritation:	0.04
Respiratory Toxicity:	0.52

Download Data

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

Natural Product: NPC101012

Natural Product ID:	NPC101012
*Common Name:**	Rel-Plicatilisin B
IUPAC Name:	(3R,3aR,5aR,8S)-8,10-dihydroxy-9-(hydroxymethyl)-3a,5a-dimethyl-3-propan-2-yl-3,4,5,6,7,8-hexahydro-1H-benzo[f]azulen-2-one
Synonyms:	Rel-Plicatilisin B
Standard InCHIKey:	PCSZVWIDBZFNQB-QHERXFFYSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-11(2)16-15(23)9-13-18(24)17-12(10-21)14(22)5-6-19(17,3)7-8-20(13,16)4/h11,14,16,21-22,24H,5-10H2,1-4H3/t14-,16-,19-,20-/m0/s1
SMILES:	CC(C)[C@H]1C(=O)CC2=C(C3=C(CO)[C@H](CC[C@@]3(C)CC[C@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2057716
PubChem CID:	62707592
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001661] Secondary alcohols

*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
NPO32901	coprinus plicatilis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22749279]

☑ 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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	25900.0	nM	PMID[492982]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000.0	nM	PMID[492982]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[492982]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	50000.0	nM	PMID[492982]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	38900.0	nM	PMID[492982]
NPT1045	Cell Line	U2OS	Homo sapiens	IC50	>	50000.0	nM	PMID[492982]

☑ 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 NPC101012 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	156
0.1-0.2	1105
0.2-0.3	5575
0.3-0.4	16074
0.4-0.5	9868
0.5-0.6	7150
0.6-0.7	2534
0.7-0.8	233
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7931	Intermediate Similarity	NPC287079
0.7889	Intermediate Similarity	NPC472942
0.7831	Intermediate Similarity	NPC229204
0.7802	Intermediate Similarity	NPC474690
0.7753	Intermediate Similarity	NPC214387
0.7738	Intermediate Similarity	NPC306095
0.7717	Intermediate Similarity	NPC180950
0.7711	Intermediate Similarity	NPC475994
0.7711	Intermediate Similarity	NPC297996
0.7701	Intermediate Similarity	NPC471224
0.7701	Intermediate Similarity	NPC474083
0.7692	Intermediate Similarity	NPC472930
0.7692	Intermediate Similarity	NPC477520
0.7692	Intermediate Similarity	NPC45264
0.7683	Intermediate Similarity	NPC469646
0.7667	Intermediate Similarity	NPC477149
0.7667	Intermediate Similarity	NPC69622
0.7667	Intermediate Similarity	NPC477147
0.7647	Intermediate Similarity	NPC136150
0.764	Intermediate Similarity	NPC44181
0.7629	Intermediate Similarity	NPC121099
0.7619	Intermediate Similarity	NPC7232
0.7609	Intermediate Similarity	NPC299100
0.7609	Intermediate Similarity	NPC469406
0.759	Intermediate Similarity	NPC74995
0.7582	Intermediate Similarity	NPC107690
0.7558	Intermediate Similarity	NPC311092
0.7556	Intermediate Similarity	NPC123912
0.7553	Intermediate Similarity	NPC474785
0.7553	Intermediate Similarity	NPC474938
0.7529	Intermediate Similarity	NPC157895
0.7529	Intermediate Similarity	NPC148685
0.7529	Intermediate Similarity	NPC45495
0.7529	Intermediate Similarity	NPC104120
0.7528	Intermediate Similarity	NPC220930
0.7528	Intermediate Similarity	NPC272039
0.75	Intermediate Similarity	NPC197823
0.75	Intermediate Similarity	NPC470254
0.7473	Intermediate Similarity	NPC48010
0.747	Intermediate Similarity	NPC279537
0.7447	Intermediate Similarity	NPC301534
0.7447	Intermediate Similarity	NPC250757
0.7444	Intermediate Similarity	NPC292491
0.7444	Intermediate Similarity	NPC310752
0.7442	Intermediate Similarity	NPC4166
0.7419	Intermediate Similarity	NPC184870
0.7416	Intermediate Similarity	NPC89077
0.7416	Intermediate Similarity	NPC469994
0.7416	Intermediate Similarity	NPC322159
0.7412	Intermediate Similarity	NPC152061
0.7412	Intermediate Similarity	NPC281138
0.7412	Intermediate Similarity	NPC308038
0.7396	Intermediate Similarity	NPC477521
0.7391	Intermediate Similarity	NPC233116
0.7391	Intermediate Similarity	NPC473998
0.7391	Intermediate Similarity	NPC63748
0.7386	Intermediate Similarity	NPC7927
0.7386	Intermediate Similarity	NPC230527
0.7386	Intermediate Similarity	NPC165064
0.7386	Intermediate Similarity	NPC227132
0.7381	Intermediate Similarity	NPC86917
0.7368	Intermediate Similarity	NPC161147
0.7363	Intermediate Similarity	NPC31985
0.7363	Intermediate Similarity	NPC472970
0.7363	Intermediate Similarity	NPC472971
0.7363	Intermediate Similarity	NPC77263
0.7363	Intermediate Similarity	NPC309603
0.7363	Intermediate Similarity	NPC250592
0.7363	Intermediate Similarity	NPC473999
0.7363	Intermediate Similarity	NPC2983
0.7363	Intermediate Similarity	NPC1015
0.7356	Intermediate Similarity	NPC151519
0.7349	Intermediate Similarity	NPC474011
0.734	Intermediate Similarity	NPC469995
0.734	Intermediate Similarity	NPC174948
0.734	Intermediate Similarity	NPC297199
0.734	Intermediate Similarity	NPC472932
0.734	Intermediate Similarity	NPC173875
0.734	Intermediate Similarity	NPC318282
0.734	Intermediate Similarity	NPC37646
0.7333	Intermediate Similarity	NPC138756
0.7333	Intermediate Similarity	NPC141292
0.7333	Intermediate Similarity	NPC317590
0.7333	Intermediate Similarity	NPC90652
0.7333	Intermediate Similarity	NPC136548
0.7326	Intermediate Similarity	NPC172013
0.732	Intermediate Similarity	NPC282524
0.732	Intermediate Similarity	NPC115899
0.7317	Intermediate Similarity	NPC186042
0.7312	Intermediate Similarity	NPC69454
0.7303	Intermediate Similarity	NPC470574
0.7303	Intermediate Similarity	NPC179006
0.7303	Intermediate Similarity	NPC474853
0.7292	Intermediate Similarity	NPC166745
0.7292	Intermediate Similarity	NPC235464
0.7292	Intermediate Similarity	NPC48647
0.7292	Intermediate Similarity	NPC471717
0.7292	Intermediate Similarity	NPC103051
0.7283	Intermediate Similarity	NPC230332
0.7283	Intermediate Similarity	NPC469400
0.7283	Intermediate Similarity	NPC320026
0.7273	Intermediate Similarity	NPC105173
0.7273	Intermediate Similarity	NPC86370
0.7273	Intermediate Similarity	NPC278648
0.7273	Intermediate Similarity	NPC476082
0.7263	Intermediate Similarity	NPC40765
0.7263	Intermediate Similarity	NPC7124
0.7263	Intermediate Similarity	NPC328371
0.7263	Intermediate Similarity	NPC472941
0.7263	Intermediate Similarity	NPC3772
0.7263	Intermediate Similarity	NPC249954
0.7263	Intermediate Similarity	NPC456
0.7263	Intermediate Similarity	NPC243525
0.7263	Intermediate Similarity	NPC155676
0.7262	Intermediate Similarity	NPC263582
0.7253	Intermediate Similarity	NPC476796
0.7253	Intermediate Similarity	NPC470417
0.725	Intermediate Similarity	NPC167527
0.7241	Intermediate Similarity	NPC6663
0.7241	Intermediate Similarity	NPC470241
0.7234	Intermediate Similarity	NPC292793
0.7234	Intermediate Similarity	NPC8993
0.7234	Intermediate Similarity	NPC474882
0.7234	Intermediate Similarity	NPC473162
0.7222	Intermediate Similarity	NPC472986
0.7222	Intermediate Similarity	NPC472974
0.7222	Intermediate Similarity	NPC472985
0.7222	Intermediate Similarity	NPC470955
0.7222	Intermediate Similarity	NPC473168
0.7222	Intermediate Similarity	NPC72133
0.7222	Intermediate Similarity	NPC473226
0.7222	Intermediate Similarity	NPC198761
0.7222	Intermediate Similarity	NPC194417
0.7216	Intermediate Similarity	NPC266955
0.7209	Intermediate Similarity	NPC472490
0.7209	Intermediate Similarity	NPC246458
0.7209	Intermediate Similarity	NPC474113
0.7204	Intermediate Similarity	NPC45269
0.7204	Intermediate Similarity	NPC155304
0.7204	Intermediate Similarity	NPC475806
0.7204	Intermediate Similarity	NPC19114
0.7204	Intermediate Similarity	NPC472978
0.7191	Intermediate Similarity	NPC473157
0.7191	Intermediate Similarity	NPC85774
0.7191	Intermediate Similarity	NPC82902
0.7191	Intermediate Similarity	NPC473246
0.7191	Intermediate Similarity	NPC161423
0.7191	Intermediate Similarity	NPC227064
0.7191	Intermediate Similarity	NPC295799
0.7191	Intermediate Similarity	NPC321187
0.7191	Intermediate Similarity	NPC58841
0.7191	Intermediate Similarity	NPC59453
0.7191	Intermediate Similarity	NPC221758
0.7191	Intermediate Similarity	NPC214043
0.7191	Intermediate Similarity	NPC329043
0.7188	Intermediate Similarity	NPC472073
0.7188	Intermediate Similarity	NPC472074
0.7188	Intermediate Similarity	NPC106557
0.7188	Intermediate Similarity	NPC18319
0.7188	Intermediate Similarity	NPC320306
0.7188	Intermediate Similarity	NPC53844
0.7188	Intermediate Similarity	NPC122294
0.7188	Intermediate Similarity	NPC471815
0.7188	Intermediate Similarity	NPC253826
0.7188	Intermediate Similarity	NPC121339
0.7176	Intermediate Similarity	NPC197659
0.7176	Intermediate Similarity	NPC137547
0.7174	Intermediate Similarity	NPC84271
0.7174	Intermediate Similarity	NPC474704
0.7174	Intermediate Similarity	NPC472983
0.7174	Intermediate Similarity	NPC475921
0.7174	Intermediate Similarity	NPC32830
0.7174	Intermediate Similarity	NPC102414
0.7174	Intermediate Similarity	NPC469319
0.7174	Intermediate Similarity	NPC155479
0.7174	Intermediate Similarity	NPC473100
0.7174	Intermediate Similarity	NPC229871
0.7174	Intermediate Similarity	NPC212664
0.7174	Intermediate Similarity	NPC474245
0.7174	Intermediate Similarity	NPC77168
0.7172	Intermediate Similarity	NPC475050
0.716	Intermediate Similarity	NPC469677
0.7159	Intermediate Similarity	NPC93590
0.7158	Intermediate Similarity	NPC259286
0.7158	Intermediate Similarity	NPC271195
0.7158	Intermediate Similarity	NPC88310
0.7158	Intermediate Similarity	NPC280725
0.7143	Intermediate Similarity	NPC475740
0.7143	Intermediate Similarity	NPC469317
0.7143	Intermediate Similarity	NPC241875
0.7143	Intermediate Similarity	NPC114236
0.7143	Intermediate Similarity	NPC99909
0.7143	Intermediate Similarity	NPC469314
0.7128	Intermediate Similarity	NPC152897
0.7128	Intermediate Similarity	NPC109305
0.7128	Intermediate Similarity	NPC66429
0.7128	Intermediate Similarity	NPC243866
0.7128	Intermediate Similarity	NPC474736
0.7126	Intermediate Similarity	NPC472478
0.7113	Intermediate Similarity	NPC10364

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 NPC101012 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	147
0.1-0.2	1735
0.2-0.3	4098
0.3-0.4	2296
0.4-0.5	488
0.5-0.6	250
0.6-0.7	131
0.7-0.8	5
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
0.75	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5279	Phase 3
0.7356	Intermediate Similarity	NPD3667	Approved
0.7222	Intermediate Similarity	NPD3618	Phase 1
0.7191	Intermediate Similarity	NPD3666	Approved
0.7191	Intermediate Similarity	NPD4786	Approved
0.7191	Intermediate Similarity	NPD3665	Phase 1
0.7191	Intermediate Similarity	NPD3133	Approved
0.7093	Intermediate Similarity	NPD3617	Approved
0.6989	Remote Similarity	NPD5328	Approved
0.6989	Remote Similarity	NPD4753	Phase 2
0.6966	Remote Similarity	NPD4270	Approved
0.6966	Remote Similarity	NPD4269	Approved
0.69	Remote Similarity	NPD5211	Phase 2
0.6889	Remote Similarity	NPD5362	Discontinued
0.6889	Remote Similarity	NPD7154	Phase 3
0.6842	Remote Similarity	NPD6079	Approved
0.6842	Remote Similarity	NPD7637	Suspended
0.6837	Remote Similarity	NPD4755	Approved
0.6818	Remote Similarity	NPD6929	Approved
0.6813	Remote Similarity	NPD3668	Phase 3
0.6782	Remote Similarity	NPD5776	Phase 2
0.6782	Remote Similarity	NPD6925	Approved
0.6771	Remote Similarity	NPD5779	Approved
0.6771	Remote Similarity	NPD5778	Approved
0.6771	Remote Similarity	NPD4202	Approved
0.6765	Remote Similarity	NPD5141	Approved
0.6742	Remote Similarity	NPD6930	Phase 2
0.6742	Remote Similarity	NPD4822	Approved
0.6742	Remote Similarity	NPD4820	Approved
0.6742	Remote Similarity	NPD6931	Approved
0.6742	Remote Similarity	NPD4821	Approved
0.6742	Remote Similarity	NPD4252	Approved
0.6742	Remote Similarity	NPD7514	Phase 3
0.6742	Remote Similarity	NPD5368	Approved
0.6742	Remote Similarity	NPD4819	Approved
0.6739	Remote Similarity	NPD1696	Phase 3
0.6739	Remote Similarity	NPD5363	Approved
0.6737	Remote Similarity	NPD5785	Approved
0.6735	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5221	Approved
0.6735	Remote Similarity	NPD5222	Approved
0.6735	Remote Similarity	NPD4697	Phase 3
0.6705	Remote Similarity	NPD7145	Approved
0.6705	Remote Similarity	NPD4268	Approved
0.6705	Remote Similarity	NPD4271	Approved
0.6703	Remote Similarity	NPD6695	Phase 3
0.67	Remote Similarity	NPD5286	Approved
0.67	Remote Similarity	NPD5285	Approved
0.67	Remote Similarity	NPD4696	Approved
0.67	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD5786	Approved
0.6667	Remote Similarity	NPD6902	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6633	Remote Similarity	NPD4629	Approved
0.6633	Remote Similarity	NPD5210	Approved
0.663	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6924	Approved
0.6628	Remote Similarity	NPD6926	Approved
0.6598	Remote Similarity	NPD6399	Phase 3
0.6593	Remote Similarity	NPD4221	Approved
0.6593	Remote Similarity	NPD4223	Phase 3
0.6593	Remote Similarity	NPD6435	Approved
0.6569	Remote Similarity	NPD5224	Approved
0.6569	Remote Similarity	NPD4633	Approved
0.6569	Remote Similarity	NPD5225	Approved
0.6569	Remote Similarity	NPD5226	Approved
0.6556	Remote Similarity	NPD7332	Phase 2
0.6556	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4695	Discontinued
0.6556	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8264	Approved
0.6548	Remote Similarity	NPD6923	Approved
0.6548	Remote Similarity	NPD6922	Approved
0.6526	Remote Similarity	NPD4518	Approved
0.6522	Remote Similarity	NPD5332	Approved
0.6522	Remote Similarity	NPD5331	Approved
0.6522	Remote Similarity	NPD4788	Approved
0.6517	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5175	Approved
0.6505	Remote Similarity	NPD5174	Approved
0.65	Remote Similarity	NPD6084	Phase 2
0.65	Remote Similarity	NPD6083	Phase 2
0.6495	Remote Similarity	NPD5281	Approved
0.6495	Remote Similarity	NPD5284	Approved
0.6495	Remote Similarity	NPD7515	Phase 2
0.6489	Remote Similarity	NPD4519	Discontinued
0.6489	Remote Similarity	NPD4623	Approved
0.6484	Remote Similarity	NPD4790	Discontinued
0.6484	Remote Similarity	NPD5369	Approved
0.6477	Remote Similarity	NPD6933	Approved
0.6471	Remote Similarity	NPD7144	Approved
0.6471	Remote Similarity	NPD5223	Approved
0.6471	Remote Similarity	NPD7143	Approved
0.6465	Remote Similarity	NPD5695	Phase 3
0.6463	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD7341	Phase 2
0.6458	Remote Similarity	NPD6101	Approved
0.6458	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD4197	Approved
0.6421	Remote Similarity	NPD7524	Approved
0.6421	Remote Similarity	NPD7750	Discontinued
0.6404	Remote Similarity	NPD6932	Approved
0.6395	Remote Similarity	NPD5276	Approved
0.6395	Remote Similarity	NPD7151	Approved
0.6395	Remote Similarity	NPD7152	Approved
0.6395	Remote Similarity	NPD7150	Approved
0.6392	Remote Similarity	NPD4096	Approved
0.6386	Remote Similarity	NPD3704	Approved
0.6383	Remote Similarity	NPD5329	Approved
0.6383	Remote Similarity	NPD6893	Approved
0.6383	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6402	Approved
0.6381	Remote Similarity	NPD5739	Approved
0.6381	Remote Similarity	NPD6675	Approved
0.6381	Remote Similarity	NPD4767	Approved
0.6381	Remote Similarity	NPD7128	Approved
0.6381	Remote Similarity	NPD4768	Approved
0.6373	Remote Similarity	NPD7639	Approved
0.6373	Remote Similarity	NPD7640	Approved
0.6364	Remote Similarity	NPD8039	Approved
0.6353	Remote Similarity	NPD3698	Phase 2
0.6353	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD4754	Approved
0.6321	Remote Similarity	NPD5701	Approved
0.6321	Remote Similarity	NPD5697	Approved
0.6316	Remote Similarity	NPD4688	Approved
0.6316	Remote Similarity	NPD7334	Approved
0.6316	Remote Similarity	NPD4693	Phase 3
0.6316	Remote Similarity	NPD4249	Approved
0.6316	Remote Similarity	NPD4689	Approved
0.6316	Remote Similarity	NPD4690	Approved
0.6316	Remote Similarity	NPD7521	Approved
0.6316	Remote Similarity	NPD5690	Phase 2
0.6316	Remote Similarity	NPD5205	Approved
0.6316	Remote Similarity	NPD5330	Approved
0.6316	Remote Similarity	NPD4138	Approved
0.6316	Remote Similarity	NPD7146	Approved
0.6316	Remote Similarity	NPD6684	Approved
0.6316	Remote Similarity	NPD6409	Approved
0.6304	Remote Similarity	NPD6898	Phase 1
0.6296	Remote Similarity	NPD368	Approved
0.6292	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD4244	Approved
0.6279	Remote Similarity	NPD4245	Approved
0.6275	Remote Similarity	NPD7638	Approved
0.6275	Remote Similarity	NPD5696	Approved
0.6264	Remote Similarity	NPD6683	Phase 2
0.6263	Remote Similarity	NPD5133	Approved
0.6262	Remote Similarity	NPD4730	Approved
0.6262	Remote Similarity	NPD5128	Approved
0.6262	Remote Similarity	NPD7320	Approved
0.6262	Remote Similarity	NPD6899	Approved
0.6262	Remote Similarity	NPD6881	Approved
0.6262	Remote Similarity	NPD4729	Approved
0.625	Remote Similarity	NPD4250	Approved
0.625	Remote Similarity	NPD4058	Approved
0.625	Remote Similarity	NPD7632	Discontinued
0.625	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD5733	Approved
0.625	Remote Similarity	NPD4687	Approved
0.625	Remote Similarity	NPD4251	Approved
0.6226	Remote Similarity	NPD7333	Discontinued
0.6222	Remote Similarity	NPD4756	Discovery
0.6211	Remote Similarity	NPD1694	Approved
0.6207	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6014	Approved
0.6204	Remote Similarity	NPD6013	Approved
0.6204	Remote Similarity	NPD6372	Approved
0.6204	Remote Similarity	NPD6012	Approved
0.6204	Remote Similarity	NPD6373	Approved
0.62	Remote Similarity	NPD5282	Discontinued
0.62	Remote Similarity	NPD7748	Approved
0.6196	Remote Similarity	NPD7525	Registered
0.619	Remote Similarity	NPD7331	Phase 2
0.6186	Remote Similarity	NPD5737	Approved
0.6186	Remote Similarity	NPD6903	Approved
0.6186	Remote Similarity	NPD6672	Approved
0.6186	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6942	Approved
0.618	Remote Similarity	NPD3703	Phase 2
0.618	Remote Similarity	NPD7339	Approved
0.6168	Remote Similarity	NPD6412	Phase 2
0.6163	Remote Similarity	NPD4137	Phase 3
0.6162	Remote Similarity	NPD7087	Discontinued
0.6162	Remote Similarity	NPD7983	Approved
0.6147	Remote Similarity	NPD5251	Approved
0.6147	Remote Similarity	NPD5248	Approved
0.6147	Remote Similarity	NPD6883	Approved
0.6147	Remote Similarity	NPD7290	Approved
0.6147	Remote Similarity	NPD5247	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