NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	268.17
Volume:	280.771
LogP:	1.697
LogD:	1.524
LogS:	-2.915
# Rotatable Bonds:	1
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	5.181
Fsp3:	0.867
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:	-5.058
MDCK Permeability:	1.160991087090224e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.771
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.014
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.889
Plasma Protein Binding (PPB):	43.50945281982422%
Volume Distribution (VD):	0.669
Pgp-substrate:	59.019935607910156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.897
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.054
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.369
CYP3A4-substrate:	0.696

ADMET: Excretion

Clearance (CL):	6.389
Half-life (T1/2):	0.673

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.558
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.155
Maximum Recommended Daily Dose:	0.098
Skin Sensitization:	0.138
Carcinogencity:	0.13
Eye Corrosion:	0.047
Eye Irritation:	0.451
Respiratory Toxicity:	0.808

Download Data

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

Natural Product: NPC311102

Natural Product ID:	NPC311102
*Common Name:**	Rel-Calamusin D
IUPAC Name:	(1S,4R,5S,8S)-4,8-dihydroxy-1,8-dimethyl-4-propan-2-ylspiro[4.5]decane-3,9-dione
Synonyms:	Rel-Calamusin D
Standard InCHIKey:	FAIWITAHODURJZ-HJPIBITLSA-N
Standard InCHI:	InChI=1S/C15H24O4/c1-9(2)15(19)11(16)7-10(3)14(15)6-5-13(4,18)12(17)8-14/h9-10,18-19H,5-8H2,1-4H3/t10-,13-,14-,15-/m0/s1
SMILES:	CC(C)[C@@]1(C(=O)C[C@H](C)[C@]21CC[C@@](C)(C(=O)C2)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063012
PubChem CID:	60156053
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0002088] Acyloins

*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
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21563811]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22671987]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23373216]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25682	Acorus calamus	Species	Acoraceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	>	10000.0	nM	PMID[512924]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[512924]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[512924]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[512924]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[512924]

☑ 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 NPC311102 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	319
0.1-0.2	4378
0.2-0.3	15363
0.3-0.4	10469
0.4-0.5	7815
0.5-0.6	3727
0.6-0.7	603
0.7-0.8	22
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7763	Intermediate Similarity	NPC155441
0.775	Intermediate Similarity	NPC328007
0.7647	Intermediate Similarity	NPC476296
0.7625	Intermediate Similarity	NPC254123
0.7619	Intermediate Similarity	NPC191221
0.759	Intermediate Similarity	NPC476726
0.759	Intermediate Similarity	NPC476727
0.7439	Intermediate Similarity	NPC327451
0.7375	Intermediate Similarity	NPC472310
0.7361	Intermediate Similarity	NPC128608
0.7317	Intermediate Similarity	NPC317066
0.7308	Intermediate Similarity	NPC132064
0.7284	Intermediate Similarity	NPC470609
0.7253	Intermediate Similarity	NPC476294
0.7229	Intermediate Similarity	NPC472847
0.7179	Intermediate Similarity	NPC133922
0.7143	Intermediate Similarity	NPC472309
0.7125	Intermediate Similarity	NPC169389
0.7108	Intermediate Similarity	NPC271163
0.7105	Intermediate Similarity	NPC98711
0.7089	Intermediate Similarity	NPC35871
0.7089	Intermediate Similarity	NPC159789
0.7089	Intermediate Similarity	NPC472311
0.7089	Intermediate Similarity	NPC68565
0.7027	Intermediate Similarity	NPC469791
0.7011	Intermediate Similarity	NPC90676
0.7	Intermediate Similarity	NPC472486
0.7	Intermediate Similarity	NPC472487
0.6988	Remote Similarity	NPC469745
0.6977	Remote Similarity	NPC472272
0.6974	Remote Similarity	NPC473225
0.6962	Remote Similarity	NPC472854
0.6962	Remote Similarity	NPC254340
0.6941	Remote Similarity	NPC291310
0.6941	Remote Similarity	NPC50438
0.6905	Remote Similarity	NPC268040
0.6883	Remote Similarity	NPC324607
0.6883	Remote Similarity	NPC321732
0.6875	Remote Similarity	NPC125767
0.6875	Remote Similarity	NPC21220
0.6848	Remote Similarity	NPC476728
0.6848	Remote Similarity	NPC49371
0.6835	Remote Similarity	NPC310766
0.6829	Remote Similarity	NPC185465
0.6818	Remote Similarity	NPC477614
0.6818	Remote Similarity	NPC471941
0.6818	Remote Similarity	NPC226491
0.6813	Remote Similarity	NPC470424
0.6782	Remote Similarity	NPC80700
0.6782	Remote Similarity	NPC248216
0.6778	Remote Similarity	NPC474065
0.6774	Remote Similarity	NPC477267
0.6774	Remote Similarity	NPC472689
0.6774	Remote Similarity	NPC477268
0.6774	Remote Similarity	NPC472690
0.6753	Remote Similarity	NPC319007
0.6753	Remote Similarity	NPC470956
0.675	Remote Similarity	NPC215030
0.6747	Remote Similarity	NPC320144
0.6744	Remote Similarity	NPC475689
0.6742	Remote Similarity	NPC61688
0.6739	Remote Similarity	NPC305808
0.6735	Remote Similarity	NPC165873
0.6711	Remote Similarity	NPC268736
0.6711	Remote Similarity	NPC477931
0.6709	Remote Similarity	NPC151018
0.6709	Remote Similarity	NPC320549
0.6709	Remote Similarity	NPC58057
0.6709	Remote Similarity	NPC89310
0.6709	Remote Similarity	NPC156277
0.6707	Remote Similarity	NPC477919
0.6707	Remote Similarity	NPC23884
0.6707	Remote Similarity	NPC112463
0.6707	Remote Similarity	NPC221420
0.6707	Remote Similarity	NPC74685
0.6707	Remote Similarity	NPC214030
0.6707	Remote Similarity	NPC180199
0.6707	Remote Similarity	NPC83108
0.6706	Remote Similarity	NPC30583
0.6705	Remote Similarity	NPC263802
0.6703	Remote Similarity	NPC161035
0.6703	Remote Similarity	NPC476189
0.6703	Remote Similarity	NPC233118
0.6702	Remote Similarity	NPC253995
0.6667	Remote Similarity	NPC6120
0.6667	Remote Similarity	NPC196197
0.6667	Remote Similarity	NPC46758
0.6667	Remote Similarity	NPC477851
0.6667	Remote Similarity	NPC27349
0.6667	Remote Similarity	NPC327728
0.6667	Remote Similarity	NPC316930
0.6667	Remote Similarity	NPC473350
0.6667	Remote Similarity	NPC131892
0.6667	Remote Similarity	NPC213178
0.6667	Remote Similarity	NPC475062
0.6667	Remote Similarity	NPC472853
0.6667	Remote Similarity	NPC100313
0.6667	Remote Similarity	NPC24014
0.6632	Remote Similarity	NPC156324
0.6632	Remote Similarity	NPC474720
0.6632	Remote Similarity	NPC55503
0.663	Remote Similarity	NPC76136
0.663	Remote Similarity	NPC329713
0.663	Remote Similarity	NPC470423
0.663	Remote Similarity	NPC217567
0.6629	Remote Similarity	NPC236459
0.6628	Remote Similarity	NPC472492
0.6627	Remote Similarity	NPC199965
0.6627	Remote Similarity	NPC171426
0.6627	Remote Similarity	NPC476732
0.6627	Remote Similarity	NPC478084
0.6627	Remote Similarity	NPC34046
0.6627	Remote Similarity	NPC224802
0.6627	Remote Similarity	NPC80089
0.6627	Remote Similarity	NPC324700
0.6625	Remote Similarity	NPC232112
0.66	Remote Similarity	NPC320475
0.66	Remote Similarity	NPC321661
0.6598	Remote Similarity	NPC266
0.6598	Remote Similarity	NPC191892
0.6593	Remote Similarity	NPC474699
0.6593	Remote Similarity	NPC52756
0.6591	Remote Similarity	NPC243746
0.6591	Remote Similarity	NPC474448
0.6585	Remote Similarity	NPC5767
0.6585	Remote Similarity	NPC25908
0.6585	Remote Similarity	NPC124289
0.6585	Remote Similarity	NPC475742
0.6585	Remote Similarity	NPC115719
0.6585	Remote Similarity	NPC142759
0.6585	Remote Similarity	NPC473437
0.6585	Remote Similarity	NPC141346
0.6582	Remote Similarity	NPC163020
0.6582	Remote Similarity	NPC108131
0.6562	Remote Similarity	NPC298266
0.6562	Remote Similarity	NPC259654
0.6559	Remote Similarity	NPC287354
0.6559	Remote Similarity	NPC62407
0.6559	Remote Similarity	NPC470031
0.6556	Remote Similarity	NPC97032
0.6552	Remote Similarity	NPC472480
0.6552	Remote Similarity	NPC144258
0.6548	Remote Similarity	NPC201276
0.6548	Remote Similarity	NPC80891
0.6548	Remote Similarity	NPC245029
0.6548	Remote Similarity	NPC31302
0.6543	Remote Similarity	NPC477867
0.6533	Remote Similarity	NPC209686
0.6533	Remote Similarity	NPC249078
0.6533	Remote Similarity	NPC236099
0.6531	Remote Similarity	NPC88469
0.6531	Remote Similarity	NPC327093
0.6517	Remote Similarity	NPC239938
0.6517	Remote Similarity	NPC153604
0.6506	Remote Similarity	NPC264602
0.6506	Remote Similarity	NPC70996
0.6506	Remote Similarity	NPC474404
0.6506	Remote Similarity	NPC475031
0.65	Remote Similarity	NPC469508
0.65	Remote Similarity	NPC473267
0.6495	Remote Similarity	NPC272472
0.6494	Remote Similarity	NPC42060
0.6489	Remote Similarity	NPC140242
0.6484	Remote Similarity	NPC77756
0.6479	Remote Similarity	NPC45387
0.6477	Remote Similarity	NPC477445
0.6477	Remote Similarity	NPC224345
0.6471	Remote Similarity	NPC164218
0.6471	Remote Similarity	NPC164999
0.6463	Remote Similarity	NPC273366
0.6463	Remote Similarity	NPC97534
0.6463	Remote Similarity	NPC174964
0.6463	Remote Similarity	NPC195155
0.6463	Remote Similarity	NPC72444
0.6458	Remote Similarity	NPC15390
0.6456	Remote Similarity	NPC474962
0.6456	Remote Similarity	NPC475952
0.6452	Remote Similarity	NPC280804
0.6437	Remote Similarity	NPC472498
0.6437	Remote Similarity	NPC217559
0.6437	Remote Similarity	NPC157328
0.6437	Remote Similarity	NPC292458
0.6437	Remote Similarity	NPC268578
0.6429	Remote Similarity	NPC475725
0.6429	Remote Similarity	NPC251017
0.6429	Remote Similarity	NPC117185
0.6421	Remote Similarity	NPC18509
0.642	Remote Similarity	NPC248567
0.6413	Remote Similarity	NPC476168
0.641	Remote Similarity	NPC478180
0.641	Remote Similarity	NPC130459
0.641	Remote Similarity	NPC472984
0.641	Remote Similarity	NPC474221
0.6404	Remote Similarity	NPC476730
0.6404	Remote Similarity	NPC472494
0.6404	Remote Similarity	NPC302111
0.6404	Remote Similarity	NPC92139
0.6404	Remote Similarity	NPC472491
0.6404	Remote Similarity	NPC120395
0.6404	Remote Similarity	NPC232156

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 NPC311102 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	435
0.1-0.2	4397
0.2-0.3	3057
0.3-0.4	708
0.4-0.5	309
0.5-0.6	179
0.6-0.7	65
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
0.72	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD5360	Phase 3
0.7143	Intermediate Similarity	NPD6081	Approved
0.7089	Intermediate Similarity	NPD3703	Phase 2
0.7027	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD4789	Approved
0.6923	Remote Similarity	NPD4758	Discontinued
0.6883	Remote Similarity	NPD3698	Phase 2
0.6875	Remote Similarity	NPD3702	Approved
0.6795	Remote Similarity	NPD4245	Approved
0.6795	Remote Similarity	NPD4244	Approved
0.6711	Remote Similarity	NPD4224	Phase 2
0.6709	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6114	Approved
0.6627	Remote Similarity	NPD6115	Approved
0.6627	Remote Similarity	NPD6697	Approved
0.6627	Remote Similarity	NPD5364	Discontinued
0.6627	Remote Similarity	NPD6118	Approved
0.6571	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD1700	Approved
0.6559	Remote Similarity	NPD5210	Approved
0.6559	Remote Similarity	NPD4629	Approved
0.6552	Remote Similarity	NPD4197	Approved
0.6477	Remote Similarity	NPD5329	Approved
0.6421	Remote Similarity	NPD4755	Approved
0.6404	Remote Similarity	NPD5280	Approved
0.6404	Remote Similarity	NPD5690	Phase 2
0.6404	Remote Similarity	NPD4694	Approved
0.6395	Remote Similarity	NPD4692	Approved
0.6395	Remote Similarity	NPD4139	Approved
0.6386	Remote Similarity	NPD6117	Approved
0.6374	Remote Similarity	NPD4753	Phase 2
0.6364	Remote Similarity	NPD388	Approved
0.6364	Remote Similarity	NPD386	Approved
0.6354	Remote Similarity	NPD5696	Approved
0.6341	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD4221	Approved
0.6322	Remote Similarity	NPD4223	Phase 3
0.631	Remote Similarity	NPD6116	Phase 1
0.6289	Remote Similarity	NPD5286	Approved
0.6289	Remote Similarity	NPD5285	Approved
0.6289	Remote Similarity	NPD4700	Approved
0.6289	Remote Similarity	NPD4696	Approved
0.625	Remote Similarity	NPD4788	Approved
0.6235	Remote Similarity	NPD3617	Approved
0.6235	Remote Similarity	NPD4238	Approved
0.6235	Remote Similarity	NPD4802	Phase 2
0.6224	Remote Similarity	NPD5223	Approved
0.6162	Remote Similarity	NPD5211	Phase 2
0.6162	Remote Similarity	NPD5226	Approved
0.6162	Remote Similarity	NPD4633	Approved
0.6162	Remote Similarity	NPD5225	Approved
0.6162	Remote Similarity	NPD5091	Approved
0.6162	Remote Similarity	NPD5224	Approved
0.6146	Remote Similarity	NPD4697	Phase 3
0.6133	Remote Similarity	NPD3198	Approved
0.61	Remote Similarity	NPD5174	Approved
0.61	Remote Similarity	NPD4754	Approved
0.61	Remote Similarity	NPD5175	Approved
0.6098	Remote Similarity	NPD5777	Approved
0.6064	Remote Similarity	NPD5281	Approved
0.6064	Remote Similarity	NPD5284	Approved
0.6058	Remote Similarity	NPD4634	Approved
0.6047	Remote Similarity	NPD3671	Phase 1
0.6044	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4138	Approved
0.6044	Remote Similarity	NPD4693	Phase 3
0.6044	Remote Similarity	NPD5205	Approved
0.6044	Remote Similarity	NPD4689	Approved
0.6044	Remote Similarity	NPD4688	Approved
0.6044	Remote Similarity	NPD4690	Approved
0.6042	Remote Similarity	NPD5695	Phase 3
0.604	Remote Similarity	NPD5141	Approved
0.6029	Remote Similarity	NPD344	Approved
0.6029	Remote Similarity	NPD345	Approved
0.6029	Remote Similarity	NPD343	Approved
0.6	Remote Similarity	NPD5133	Approved
0.598	Remote Similarity	NPD6675	Approved
0.598	Remote Similarity	NPD7128	Approved
0.598	Remote Similarity	NPD5739	Approved
0.598	Remote Similarity	NPD4768	Approved
0.598	Remote Similarity	NPD6402	Approved
0.598	Remote Similarity	NPD4767	Approved
0.5979	Remote Similarity	NPD5221	Approved
0.5979	Remote Similarity	NPD5222	Approved
0.5979	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5962	Remote Similarity	NPD6373	Approved
0.5962	Remote Similarity	NPD6372	Approved
0.5922	Remote Similarity	NPD5697	Approved
0.5922	Remote Similarity	NPD5701	Approved
0.5918	Remote Similarity	NPD5173	Approved
0.5918	Remote Similarity	NPD6084	Phase 2
0.5918	Remote Similarity	NPD6083	Phase 2
0.5888	Remote Similarity	NPD4632	Approved
0.5882	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.587	Remote Similarity	NPD6098	Approved
0.5865	Remote Similarity	NPD6899	Approved
0.5865	Remote Similarity	NPD7320	Approved
0.5865	Remote Similarity	NPD5128	Approved
0.5865	Remote Similarity	NPD6011	Approved
0.5865	Remote Similarity	NPD4730	Approved
0.5865	Remote Similarity	NPD4729	Approved
0.5865	Remote Similarity	NPD6881	Approved
0.5851	Remote Similarity	NPD6080	Approved
0.5851	Remote Similarity	NPD6673	Approved
0.5851	Remote Similarity	NPD6904	Approved
0.5851	Remote Similarity	NPD5328	Approved
0.5849	Remote Similarity	NPD6649	Approved
0.5849	Remote Similarity	NPD6650	Approved
0.5833	Remote Similarity	NPD4202	Approved
0.5824	Remote Similarity	NPD3665	Phase 1
0.5824	Remote Similarity	NPD3133	Approved
0.5824	Remote Similarity	NPD3666	Approved
0.5824	Remote Similarity	NPD4786	Approved
0.581	Remote Similarity	NPD6012	Approved
0.581	Remote Similarity	NPD6014	Approved
0.581	Remote Similarity	NPD6013	Approved
0.5789	Remote Similarity	NPD5692	Phase 3
0.5783	Remote Similarity	NPD4787	Phase 1
0.5778	Remote Similarity	NPD3667	Approved
0.5778	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD7102	Approved
0.5755	Remote Similarity	NPD5169	Approved
0.5755	Remote Similarity	NPD5250	Approved
0.5755	Remote Similarity	NPD7290	Approved
0.5755	Remote Similarity	NPD5247	Approved
0.5755	Remote Similarity	NPD5135	Approved
0.5755	Remote Similarity	NPD5249	Phase 3
0.5755	Remote Similarity	NPD5251	Approved
0.5755	Remote Similarity	NPD5248	Approved
0.5755	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD6883	Approved
0.575	Remote Similarity	NPD7341	Phase 2
0.5729	Remote Similarity	NPD6079	Approved
0.5729	Remote Similarity	NPD5693	Phase 1
0.5729	Remote Similarity	NPD5694	Approved
0.5729	Remote Similarity	NPD6050	Approved
0.5727	Remote Similarity	NPD6009	Approved
0.5701	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6847	Approved
0.5701	Remote Similarity	NPD5215	Approved
0.5701	Remote Similarity	NPD8130	Phase 1
0.5701	Remote Similarity	NPD5127	Approved
0.5701	Remote Similarity	NPD6617	Approved
0.5701	Remote Similarity	NPD5217	Approved
0.5701	Remote Similarity	NPD6869	Approved
0.5701	Remote Similarity	NPD5216	Approved
0.5699	Remote Similarity	NPD5279	Phase 3
0.5699	Remote Similarity	NPD3618	Phase 1
0.5679	Remote Similarity	NPD375	Phase 2
0.5673	Remote Similarity	NPD6008	Approved
0.567	Remote Similarity	NPD6399	Phase 3
0.5663	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD634	Phase 3
0.5648	Remote Similarity	NPD6882	Approved
0.5648	Remote Similarity	NPD8297	Approved
0.5625	Remote Similarity	NPD4096	Approved
0.5625	Remote Similarity	NPD7909	Approved
0.5618	Remote Similarity	NPD4195	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