NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.16
Volume:	269.345
LogP:	1.858
LogD:	-0.165
LogS:	-3.078
# Rotatable Bonds:	1
TPSA:	51.21
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.718
Synthetic Accessibility Score:	4.867
Fsp3:	0.8
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:	-4.626
MDCK Permeability:	2.4269791538245045e-05
Pgp-inhibitor:	0.234
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.082
30% Bioavailability (F30%):	0.629

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.915
Plasma Protein Binding (PPB):	44.91001510620117%
Volume Distribution (VD):	0.89
Pgp-substrate:	62.26075744628906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.175
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.864
CYP2C9-inhibitor:	0.026
CYP2C9-substrate:	0.206
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.303
CYP3A4-inhibitor:	0.098
CYP3A4-substrate:	0.356

ADMET: Excretion

Clearance (CL):	14.561
Half-life (T1/2):	0.879

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.208
Drug-inuced Liver Injury (DILI):	0.267
AMES Toxicity:	0.023
Rat Oral Acute Toxicity:	0.556
Maximum Recommended Daily Dose:	0.096
Skin Sensitization:	0.107
Carcinogencity:	0.167
Eye Corrosion:	0.081
Eye Irritation:	0.169
Respiratory Toxicity:	0.19

Download Data

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

Natural Product: NPC230527

Natural Product ID:	NPC230527
*Common Name:**	Rel-Calamusin F
IUPAC Name:	(1S,4R,5R,10R)-10-hydroxy-1,8-dimethyl-4-propan-2-ylspiro[4.5]dec-8-ene-3,7-dione
Synonyms:	Rel-Calamusin F
Standard InCHIKey:	JGPJOBKNJPPDNO-PUPMMZHASA-N
Standard InCHI:	InChI=1S/C15H22O3/c1-8(2)14-11(16)6-10(4)15(14)7-12(17)9(3)5-13(15)18/h5,8,10,13-14,18H,6-7H2,1-4H3/t10-,13+,14-,15-/m0/s1
SMILES:	CC([C@H]1C(=O)C[C@@H]([C@@]21CC(=O)C(=C[C@H]2O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063014
PubChem CID:	60156148
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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[543659]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	>	10000.0	nM	PMID[543659]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	10000.0	nM	PMID[543659]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[543659]
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[543659]

☑ 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 NPC230527 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	165
0.1-0.2	1162
0.2-0.3	6141
0.3-0.4	14277
0.4-0.5	10297
0.5-0.6	6446
0.6-0.7	3398
0.7-0.8	774
0.8-0.85	31
0.85-0.9	4
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC7927
0.8734	High Similarity	NPC469646
0.8605	High Similarity	NPC474854
0.8506	High Similarity	NPC123912
0.8478	Intermediate Similarity	NPC287833
0.8375	Intermediate Similarity	NPC474011
0.8313	Intermediate Similarity	NPC45495
0.8293	Intermediate Similarity	NPC475994
0.828	Intermediate Similarity	NPC51370
0.8235	Intermediate Similarity	NPC62214
0.8222	Intermediate Similarity	NPC472930
0.8222	Intermediate Similarity	NPC69454
0.8193	Intermediate Similarity	NPC7232
0.8193	Intermediate Similarity	NPC261125
0.8193	Intermediate Similarity	NPC181195
0.8171	Intermediate Similarity	NPC276769
0.8152	Intermediate Similarity	NPC472941
0.8152	Intermediate Similarity	NPC456
0.8118	Intermediate Similarity	NPC279186
0.8111	Intermediate Similarity	NPC63748
0.8095	Intermediate Similarity	NPC172013
0.809	Intermediate Similarity	NPC309603
0.809	Intermediate Similarity	NPC473999
0.8085	Intermediate Similarity	NPC476274
0.8072	Intermediate Similarity	NPC62336
0.8046	Intermediate Similarity	NPC474853
0.8046	Intermediate Similarity	NPC474083
0.8046	Intermediate Similarity	NPC471224
0.8046	Intermediate Similarity	NPC476426
0.8046	Intermediate Similarity	NPC179006
0.8043	Intermediate Similarity	NPC259286
0.8043	Intermediate Similarity	NPC472932
0.8043	Intermediate Similarity	NPC37646
0.8023	Intermediate Similarity	NPC41539
0.8023	Intermediate Similarity	NPC476082
0.8023	Intermediate Similarity	NPC65350
0.8023	Intermediate Similarity	NPC278648
0.8022	Intermediate Similarity	NPC474736
0.8	Intermediate Similarity	NPC48010
0.8	Intermediate Similarity	NPC224720
0.8	Intermediate Similarity	NPC476223
0.8	Intermediate Similarity	NPC476240
0.7979	Intermediate Similarity	NPC197386
0.7978	Intermediate Similarity	NPC328539
0.7976	Intermediate Similarity	NPC19900
0.7976	Intermediate Similarity	NPC308038
0.7959	Intermediate Similarity	NPC185
0.7957	Intermediate Similarity	NPC3772
0.7957	Intermediate Similarity	NPC243525
0.7957	Intermediate Similarity	NPC249954
0.7957	Intermediate Similarity	NPC40765
0.7955	Intermediate Similarity	NPC194417
0.7952	Intermediate Similarity	NPC471061
0.7952	Intermediate Similarity	NPC86917
0.7931	Intermediate Similarity	NPC85774
0.7931	Intermediate Similarity	NPC472326
0.7931	Intermediate Similarity	NPC473246
0.7931	Intermediate Similarity	NPC214043
0.7927	Intermediate Similarity	NPC216791
0.7917	Intermediate Similarity	NPC293753
0.7917	Intermediate Similarity	NPC87351
0.7912	Intermediate Similarity	NPC475806
0.7912	Intermediate Similarity	NPC473998
0.7907	Intermediate Similarity	NPC133844
0.7907	Intermediate Similarity	NPC38796
0.7907	Intermediate Similarity	NPC158411
0.7901	Intermediate Similarity	NPC186042
0.7889	Intermediate Similarity	NPC86319
0.7889	Intermediate Similarity	NPC232747
0.7889	Intermediate Similarity	NPC214387
0.7889	Intermediate Similarity	NPC477943
0.7889	Intermediate Similarity	NPC275740
0.7882	Intermediate Similarity	NPC164218
0.7882	Intermediate Similarity	NPC472478
0.7879	Intermediate Similarity	NPC295244
0.7872	Intermediate Similarity	NPC121339
0.7872	Intermediate Similarity	NPC106557
0.7865	Intermediate Similarity	NPC136548
0.7865	Intermediate Similarity	NPC287079
0.7849	Intermediate Similarity	NPC469995
0.7849	Intermediate Similarity	NPC271195
0.7849	Intermediate Similarity	NPC174948
0.7849	Intermediate Similarity	NPC173875
0.7849	Intermediate Similarity	NPC318282
0.7841	Intermediate Similarity	NPC202868
0.7841	Intermediate Similarity	NPC28887
0.7841	Intermediate Similarity	NPC36350
0.7841	Intermediate Similarity	NPC472940
0.7841	Intermediate Similarity	NPC472931
0.7841	Intermediate Similarity	NPC469948
0.7835	Intermediate Similarity	NPC311612
0.7835	Intermediate Similarity	NPC111323
0.7831	Intermediate Similarity	NPC263582
0.7826	Intermediate Similarity	NPC125180
0.7826	Intermediate Similarity	NPC109305
0.7816	Intermediate Similarity	NPC105173
0.7812	Intermediate Similarity	NPC472924
0.7805	Intermediate Similarity	NPC215050
0.7802	Intermediate Similarity	NPC134321
0.7802	Intermediate Similarity	NPC477149
0.7802	Intermediate Similarity	NPC477147
0.7791	Intermediate Similarity	NPC136150
0.7789	Intermediate Similarity	NPC103051
0.7789	Intermediate Similarity	NPC147954
0.7778	Intermediate Similarity	NPC143767
0.7778	Intermediate Similarity	NPC131470
0.7778	Intermediate Similarity	NPC249889
0.7778	Intermediate Similarity	NPC193843
0.7766	Intermediate Similarity	NPC328371
0.7766	Intermediate Similarity	NPC117133
0.7766	Intermediate Similarity	NPC471463
0.7765	Intermediate Similarity	NPC281138
0.7765	Intermediate Similarity	NPC472490
0.7753	Intermediate Similarity	NPC222613
0.7753	Intermediate Similarity	NPC327115
0.7753	Intermediate Similarity	NPC145879
0.7753	Intermediate Similarity	NPC183736
0.7753	Intermediate Similarity	NPC469994
0.7753	Intermediate Similarity	NPC475022
0.7753	Intermediate Similarity	NPC31564
0.7753	Intermediate Similarity	NPC474778
0.7753	Intermediate Similarity	NPC474732
0.7753	Intermediate Similarity	NPC474733
0.7753	Intermediate Similarity	NPC118648
0.775	Intermediate Similarity	NPC10758
0.775	Intermediate Similarity	NPC250928
0.7742	Intermediate Similarity	NPC8993
0.7738	Intermediate Similarity	NPC74995
0.7738	Intermediate Similarity	NPC197659
0.7732	Intermediate Similarity	NPC195290
0.7732	Intermediate Similarity	NPC473424
0.7732	Intermediate Similarity	NPC204450
0.7732	Intermediate Similarity	NPC477915
0.7732	Intermediate Similarity	NPC234892
0.7727	Intermediate Similarity	NPC329043
0.7727	Intermediate Similarity	NPC165064
0.7727	Intermediate Similarity	NPC476412
0.7727	Intermediate Similarity	NPC227064
0.7727	Intermediate Similarity	NPC470812
0.7727	Intermediate Similarity	NPC237712
0.7727	Intermediate Similarity	NPC161423
0.7727	Intermediate Similarity	NPC58841
0.7727	Intermediate Similarity	NPC321187
0.7717	Intermediate Similarity	NPC168027
0.7717	Intermediate Similarity	NPC185936
0.7717	Intermediate Similarity	NPC233116
0.7717	Intermediate Similarity	NPC19114
0.7711	Intermediate Similarity	NPC251435
0.7711	Intermediate Similarity	NPC114236
0.7701	Intermediate Similarity	NPC93590
0.7692	Intermediate Similarity	NPC170775
0.7692	Intermediate Similarity	NPC2983
0.7692	Intermediate Similarity	NPC119416
0.7692	Intermediate Similarity	NPC310236
0.7692	Intermediate Similarity	NPC186688
0.7692	Intermediate Similarity	NPC472973
0.7683	Intermediate Similarity	NPC275098
0.7674	Intermediate Similarity	NPC271104
0.7667	Intermediate Similarity	NPC93778
0.7667	Intermediate Similarity	NPC475740
0.7667	Intermediate Similarity	NPC58063
0.766	Intermediate Similarity	NPC476174
0.766	Intermediate Similarity	NPC297199
0.7653	Intermediate Similarity	NPC236390
0.7647	Intermediate Similarity	NPC472928
0.7647	Intermediate Similarity	NPC474056
0.764	Intermediate Similarity	NPC474218
0.764	Intermediate Similarity	NPC142649
0.7634	Intermediate Similarity	NPC233118
0.7634	Intermediate Similarity	NPC477520
0.7634	Intermediate Similarity	NPC474807
0.7629	Intermediate Similarity	NPC81530
0.7625	Intermediate Similarity	NPC469688
0.7619	Intermediate Similarity	NPC215481
0.7619	Intermediate Similarity	NPC242722
0.7619	Intermediate Similarity	NPC470525
0.7614	Intermediate Similarity	NPC64600
0.7609	Intermediate Similarity	NPC191684
0.7609	Intermediate Similarity	NPC183283
0.7609	Intermediate Similarity	NPC230332
0.7609	Intermediate Similarity	NPC128672
0.7609	Intermediate Similarity	NPC69622
0.7604	Intermediate Similarity	NPC166745
0.7604	Intermediate Similarity	NPC471717
0.7604	Intermediate Similarity	NPC235464
0.7586	Intermediate Similarity	NPC6663
0.7582	Intermediate Similarity	NPC471722
0.7582	Intermediate Similarity	NPC477710
0.7579	Intermediate Similarity	NPC192428
0.7576	Intermediate Similarity	NPC209502
0.7576	Intermediate Similarity	NPC204833
0.7558	Intermediate Similarity	NPC84185
0.7558	Intermediate Similarity	NPC66677
0.7558	Intermediate Similarity	NPC152061
0.7558	Intermediate Similarity	NPC471890
0.7558	Intermediate Similarity	NPC229204
0.7556	Intermediate Similarity	NPC72133
0.7556	Intermediate Similarity	NPC476043
0.7556	Intermediate Similarity	NPC472974
0.7553	Intermediate Similarity	NPC196227

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 NPC230527 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1775
0.2-0.3	4170
0.3-0.4	2172
0.4-0.5	474
0.5-0.6	200
0.6-0.7	173
0.7-0.8	30
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
0.7912	Intermediate Similarity	NPD6079	Approved
0.7889	Intermediate Similarity	NPD5328	Approved
0.7753	Intermediate Similarity	NPD3618	Phase 1
0.7727	Intermediate Similarity	NPD3133	Approved
0.7727	Intermediate Similarity	NPD3665	Phase 1
0.7727	Intermediate Similarity	NPD3666	Approved
0.766	Intermediate Similarity	NPD4629	Approved
0.766	Intermediate Similarity	NPD5210	Approved
0.7647	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5222	Approved
0.7579	Intermediate Similarity	NPD4697	Phase 3
0.7579	Intermediate Similarity	NPD5221	Approved
0.7579	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD5279	Phase 3
0.7551	Intermediate Similarity	NPD5211	Phase 2
0.7528	Intermediate Similarity	NPD4786	Approved
0.75	Intermediate Similarity	NPD5173	Approved
0.75	Intermediate Similarity	NPD3667	Approved
0.7444	Intermediate Similarity	NPD5363	Approved
0.7419	Intermediate Similarity	NPD5785	Approved
0.74	Intermediate Similarity	NPD5141	Approved
0.7347	Intermediate Similarity	NPD5286	Approved
0.7347	Intermediate Similarity	NPD5285	Approved
0.7347	Intermediate Similarity	NPD4696	Approved
0.732	Intermediate Similarity	NPD4755	Approved
0.7312	Intermediate Similarity	NPD4753	Phase 2
0.7303	Intermediate Similarity	NPD4221	Approved
0.7303	Intermediate Similarity	NPD4223	Phase 3
0.7273	Intermediate Similarity	NPD5223	Approved
0.7263	Intermediate Similarity	NPD4202	Approved
0.7253	Intermediate Similarity	NPD1696	Phase 3
0.72	Intermediate Similarity	NPD5224	Approved
0.72	Intermediate Similarity	NPD5225	Approved
0.72	Intermediate Similarity	NPD5226	Approved
0.72	Intermediate Similarity	NPD4633	Approved
0.7174	Intermediate Similarity	NPD5786	Approved
0.7174	Intermediate Similarity	NPD5690	Phase 2
0.7172	Intermediate Similarity	NPD4700	Approved
0.716	Intermediate Similarity	NPD7331	Phase 2
0.7143	Intermediate Similarity	NPD4197	Approved
0.7129	Intermediate Similarity	NPD5174	Approved
0.7129	Intermediate Similarity	NPD5175	Approved
0.7111	Intermediate Similarity	NPD4270	Approved
0.7111	Intermediate Similarity	NPD4269	Approved
0.7071	Intermediate Similarity	NPD5696	Approved
0.7065	Intermediate Similarity	NPD5329	Approved
0.7065	Intermediate Similarity	NPD1694	Approved
0.7033	Intermediate Similarity	NPD5362	Discontinued
0.6989	Remote Similarity	NPD4138	Approved
0.6989	Remote Similarity	NPD4688	Approved
0.6989	Remote Similarity	NPD4694	Approved
0.6989	Remote Similarity	NPD4689	Approved
0.6989	Remote Similarity	NPD4623	Approved
0.6989	Remote Similarity	NPD4690	Approved
0.6989	Remote Similarity	NPD4693	Phase 3
0.6989	Remote Similarity	NPD4519	Discontinued
0.6989	Remote Similarity	NPD5205	Approved
0.6989	Remote Similarity	NPD5280	Approved
0.6989	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4754	Approved
0.6939	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5697	Approved
0.6907	Remote Similarity	NPD6399	Phase 3
0.6889	Remote Similarity	NPD4252	Approved
0.6889	Remote Similarity	NPD5368	Approved
0.6857	Remote Similarity	NPD6899	Approved
0.6857	Remote Similarity	NPD4730	Approved
0.6857	Remote Similarity	NPD4729	Approved
0.6857	Remote Similarity	NPD6011	Approved
0.6857	Remote Similarity	NPD6881	Approved
0.6857	Remote Similarity	NPD5168	Approved
0.6857	Remote Similarity	NPD5128	Approved
0.6854	Remote Similarity	NPD3617	Approved
0.6848	Remote Similarity	NPD4788	Approved
0.6829	Remote Similarity	NPD7341	Phase 2
0.6827	Remote Similarity	NPD4767	Approved
0.6827	Remote Similarity	NPD6675	Approved
0.6827	Remote Similarity	NPD7128	Approved
0.6827	Remote Similarity	NPD5739	Approved
0.6827	Remote Similarity	NPD6402	Approved
0.6827	Remote Similarity	NPD4768	Approved
0.6824	Remote Similarity	NPD4747	Approved
0.6824	Remote Similarity	NPD4691	Approved
0.6822	Remote Similarity	NPD6650	Approved
0.6822	Remote Similarity	NPD6649	Approved
0.6809	Remote Similarity	NPD7146	Approved
0.6809	Remote Similarity	NPD7521	Approved
0.6809	Remote Similarity	NPD6409	Approved
0.6809	Remote Similarity	NPD7334	Approved
0.6809	Remote Similarity	NPD5330	Approved
0.6809	Remote Similarity	NPD6684	Approved
0.6804	Remote Similarity	NPD5281	Approved
0.6804	Remote Similarity	NPD5284	Approved
0.68	Remote Similarity	NPD6083	Phase 2
0.68	Remote Similarity	NPD6084	Phase 2
0.6792	Remote Similarity	NPD6373	Approved
0.6792	Remote Similarity	NPD6012	Approved
0.6792	Remote Similarity	NPD6372	Approved
0.6792	Remote Similarity	NPD6014	Approved
0.6792	Remote Similarity	NPD6013	Approved
0.6778	Remote Similarity	NPD4195	Approved
0.6774	Remote Similarity	NPD3668	Phase 3
0.6768	Remote Similarity	NPD5695	Phase 3
0.6762	Remote Similarity	NPD5701	Approved
0.6739	Remote Similarity	NPD6435	Approved
0.6729	Remote Similarity	NPD5135	Approved
0.6729	Remote Similarity	NPD5251	Approved
0.6729	Remote Similarity	NPD5250	Approved
0.6729	Remote Similarity	NPD5247	Approved
0.6729	Remote Similarity	NPD5169	Approved
0.6729	Remote Similarity	NPD5248	Approved
0.6729	Remote Similarity	NPD5249	Phase 3
0.6729	Remote Similarity	NPD7102	Approved
0.6729	Remote Similarity	NPD4634	Approved
0.6729	Remote Similarity	NPD7290	Approved
0.6729	Remote Similarity	NPD6883	Approved
0.6729	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD4137	Phase 3
0.6703	Remote Similarity	NPD4695	Discontinued
0.6699	Remote Similarity	NPD5091	Approved
0.6698	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD5217	Approved
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD6903	Approved
0.6667	Remote Similarity	NPD5215	Approved
0.6667	Remote Similarity	NPD5127	Approved
0.6667	Remote Similarity	NPD5737	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD368	Approved
0.6667	Remote Similarity	NPD6672	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6667	Remote Similarity	NPD4518	Approved
0.6667	Remote Similarity	NPD5216	Approved
0.6633	Remote Similarity	NPD7515	Phase 2
0.663	Remote Similarity	NPD4790	Discontinued
0.663	Remote Similarity	NPD5369	Approved
0.6606	Remote Similarity	NPD6882	Approved
0.6606	Remote Similarity	NPD8297	Approved
0.6591	Remote Similarity	NPD5733	Approved
0.6591	Remote Similarity	NPD4687	Approved
0.6591	Remote Similarity	NPD4058	Approved
0.6552	Remote Similarity	NPD5276	Approved
0.6545	Remote Similarity	NPD4632	Approved
0.6531	Remote Similarity	NPD4096	Approved
0.6522	Remote Similarity	NPD4822	Approved
0.6522	Remote Similarity	NPD4821	Approved
0.6522	Remote Similarity	NPD4820	Approved
0.6522	Remote Similarity	NPD4819	Approved
0.6517	Remote Similarity	NPD7339	Approved
0.6517	Remote Similarity	NPD6942	Approved
0.6514	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD7639	Approved
0.6505	Remote Similarity	NPD6404	Discontinued
0.6505	Remote Similarity	NPD7640	Approved
0.6489	Remote Similarity	NPD7154	Phase 3
0.6489	Remote Similarity	NPD6110	Phase 1
0.6486	Remote Similarity	NPD5167	Approved
0.6484	Remote Similarity	NPD4271	Approved
0.6484	Remote Similarity	NPD4268	Approved
0.6452	Remote Similarity	NPD4692	Approved
0.6452	Remote Similarity	NPD4139	Approved
0.6444	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6274	Approved
0.6429	Remote Similarity	NPD6868	Approved
0.6413	Remote Similarity	NPD6929	Approved
0.6408	Remote Similarity	NPD7638	Approved
0.6404	Remote Similarity	NPD6924	Approved
0.6404	Remote Similarity	NPD6926	Approved
0.64	Remote Similarity	NPD5133	Approved
0.64	Remote Similarity	NPD5778	Approved
0.64	Remote Similarity	NPD5779	Approved
0.6392	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD5776	Phase 2
0.6374	Remote Similarity	NPD6925	Approved
0.6372	Remote Similarity	NPD6009	Approved
0.6372	Remote Similarity	NPD6317	Approved
0.6364	Remote Similarity	NPD5207	Approved
0.6355	Remote Similarity	NPD6008	Approved
0.6354	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6930	Phase 2
0.6344	Remote Similarity	NPD6931	Approved
0.6344	Remote Similarity	NPD7514	Phase 3
0.6344	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5282	Discontinued
0.6337	Remote Similarity	NPD7748	Approved
0.6329	Remote Similarity	NPD342	Phase 1
0.6327	Remote Similarity	NPD5208	Approved
0.6322	Remote Similarity	NPD6922	Approved
0.6322	Remote Similarity	NPD6923	Approved
0.6316	Remote Similarity	NPD6335	Approved
0.6316	Remote Similarity	NPD6313	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