NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	234.16
Volume:	260.554
LogP:	4.206
LogD:	3.833
LogS:	-4.235
# Rotatable Bonds:	1
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.393
Synthetic Accessibility Score:	4.3
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.553
MDCK Permeability:	2.2931282728677616e-05
Pgp-inhibitor:	0.214
Pgp-substrate:	0.095
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.068
Plasma Protein Binding (PPB):	80.0022201538086%
Volume Distribution (VD):	1.952
Pgp-substrate:	26.26224708557129%

ADMET: Metabolism

CYP1A2-inhibitor:	0.814
CYP1A2-substrate:	0.807
CYP2C19-inhibitor:	0.814
CYP2C19-substrate:	0.886
CYP2C9-inhibitor:	0.314
CYP2C9-substrate:	0.098
CYP2D6-inhibitor:	0.286
CYP2D6-substrate:	0.318
CYP3A4-inhibitor:	0.615
CYP3A4-substrate:	0.618

ADMET: Excretion

Clearance (CL):	13.661
Half-life (T1/2):	0.294

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.248
Drug-inuced Liver Injury (DILI):	0.549
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.304
Maximum Recommended Daily Dose:	0.091
Skin Sensitization:	0.93
Carcinogencity:	0.71
Eye Corrosion:	0.924
Eye Irritation:	0.914
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC222210

Natural Product ID:	NPC222210
*Common Name:**	Gajutsulactone A
IUPAC Name:	(4aS,5R,7aS)-7a-methyl-3-propan-2-ylidene-5-prop-1-en-2-yl-4a,5,6,7-tetrahydro-4H-cyclopenta[b]pyran-2-one
Synonyms:	Gajutsulactone A
Standard InCHIKey:	ZZEKLJSJUUZCFB-WHOFXGATSA-N
Standard InCHI:	InChI=1S/C15H22O2/c1-9(2)11-6-7-15(5)13(11)8-12(10(3)4)14(16)17-15/h11,13H,1,6-8H2,2-5H3/t11-,13-,15-/m0/s1
SMILES:	CC(=C)[C@@H]1CC[C@]2([C@H]1CC(=C(C)C)C(=O)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2332425
PubChem CID:	10263441
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO17780	Curcuma heyneana	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23387824]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868158]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17780	Curcuma heyneana	Species	Zingiberaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	<	65.0	%	PMID[568921]

☑ 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 NPC222210 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	181
0.1-0.2	1305
0.2-0.3	6437
0.3-0.4	15128
0.4-0.5	9624
0.5-0.6	6543
0.6-0.7	3207
0.7-0.8	260
0.8-0.85	9
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC63445
0.9211	High Similarity	NPC47747
0.8816	High Similarity	NPC53581
0.8816	High Similarity	NPC103987
0.8125	Intermediate Similarity	NPC469617
0.7901	Intermediate Similarity	NPC469620
0.7901	Intermediate Similarity	NPC469690
0.7889	Intermediate Similarity	NPC9812
0.7875	Intermediate Similarity	NPC122264
0.7841	Intermediate Similarity	NPC290651
0.7841	Intermediate Similarity	NPC221282
0.7802	Intermediate Similarity	NPC47834
0.7765	Intermediate Similarity	NPC245434
0.775	Intermediate Similarity	NPC473223
0.7738	Intermediate Similarity	NPC53867
0.7727	Intermediate Similarity	NPC77337
0.7717	Intermediate Similarity	NPC64742
0.7717	Intermediate Similarity	NPC244411
0.7692	Intermediate Similarity	NPC469737
0.7674	Intermediate Similarity	NPC469676
0.7662	Intermediate Similarity	NPC265574
0.7647	Intermediate Similarity	NPC238197
0.764	Intermediate Similarity	NPC472953
0.7634	Intermediate Similarity	NPC280963
0.7595	Intermediate Similarity	NPC135703
0.7595	Intermediate Similarity	NPC300940
0.7582	Intermediate Similarity	NPC470974
0.7582	Intermediate Similarity	NPC470978
0.7561	Intermediate Similarity	NPC474341
0.7561	Intermediate Similarity	NPC471220
0.7553	Intermediate Similarity	NPC62670
0.7553	Intermediate Similarity	NPC116139
0.7553	Intermediate Similarity	NPC475099
0.7553	Intermediate Similarity	NPC206079
0.7528	Intermediate Similarity	NPC37607
0.7528	Intermediate Similarity	NPC301969
0.75	Intermediate Similarity	NPC10276
0.75	Intermediate Similarity	NPC78677
0.75	Intermediate Similarity	NPC35089
0.75	Intermediate Similarity	NPC59994
0.7474	Intermediate Similarity	NPC66110
0.7471	Intermediate Similarity	NPC474045
0.7471	Intermediate Similarity	NPC261253
0.747	Intermediate Similarity	NPC66677
0.747	Intermediate Similarity	NPC471890
0.747	Intermediate Similarity	NPC84185
0.747	Intermediate Similarity	NPC182550
0.7442	Intermediate Similarity	NPC14575
0.7442	Intermediate Similarity	NPC475100
0.7442	Intermediate Similarity	NPC196487
0.7442	Intermediate Similarity	NPC156485
0.7439	Intermediate Similarity	NPC187568
0.7439	Intermediate Similarity	NPC41780
0.7419	Intermediate Similarity	NPC69385
0.7412	Intermediate Similarity	NPC475936
0.7412	Intermediate Similarity	NPC133844
0.7407	Intermediate Similarity	NPC244166
0.7391	Intermediate Similarity	NPC37408
0.7386	Intermediate Similarity	NPC270270
0.7381	Intermediate Similarity	NPC233377
0.7381	Intermediate Similarity	NPC74673
0.7381	Intermediate Similarity	NPC69271
0.7381	Intermediate Similarity	NPC276356
0.7368	Intermediate Similarity	NPC477950
0.7356	Intermediate Similarity	NPC287015
0.7356	Intermediate Similarity	NPC235792
0.7356	Intermediate Similarity	NPC476628
0.7356	Intermediate Similarity	NPC474547
0.7356	Intermediate Similarity	NPC146850
0.7349	Intermediate Similarity	NPC128276
0.7349	Intermediate Similarity	NPC299235
0.734	Intermediate Similarity	NPC222011
0.7326	Intermediate Similarity	NPC193198
0.7326	Intermediate Similarity	NPC245665
0.7326	Intermediate Similarity	NPC39588
0.732	Intermediate Similarity	NPC309190
0.7317	Intermediate Similarity	NPC235906
0.7312	Intermediate Similarity	NPC118159
0.7303	Intermediate Similarity	NPC224652
0.7294	Intermediate Similarity	NPC325031
0.7283	Intermediate Similarity	NPC90453
0.7273	Intermediate Similarity	NPC67493
0.7273	Intermediate Similarity	NPC234038
0.7262	Intermediate Similarity	NPC472013
0.7262	Intermediate Similarity	NPC476624
0.7253	Intermediate Similarity	NPC478244
0.7253	Intermediate Similarity	NPC478243
0.725	Intermediate Similarity	NPC129665
0.7241	Intermediate Similarity	NPC9868
0.7241	Intermediate Similarity	NPC243618
0.7241	Intermediate Similarity	NPC149869
0.7241	Intermediate Similarity	NPC30486
0.7241	Intermediate Similarity	NPC72464
0.7241	Intermediate Similarity	NPC70424
0.7234	Intermediate Similarity	NPC477949
0.7229	Intermediate Similarity	NPC180290
0.7229	Intermediate Similarity	NPC65603
0.7229	Intermediate Similarity	NPC316500
0.7229	Intermediate Similarity	NPC107668
0.7229	Intermediate Similarity	NPC57744
0.7229	Intermediate Similarity	NPC316324
0.7229	Intermediate Similarity	NPC208223
0.7222	Intermediate Similarity	NPC305039
0.7222	Intermediate Similarity	NPC285982
0.7222	Intermediate Similarity	NPC474679
0.7222	Intermediate Similarity	NPC115179
0.7222	Intermediate Similarity	NPC232747
0.7222	Intermediate Similarity	NPC106040
0.7222	Intermediate Similarity	NPC212598
0.7209	Intermediate Similarity	NPC186276
0.7209	Intermediate Similarity	NPC35556
0.7209	Intermediate Similarity	NPC200513
0.7204	Intermediate Similarity	NPC67584
0.7204	Intermediate Similarity	NPC52044
0.7195	Intermediate Similarity	NPC475861
0.7191	Intermediate Similarity	NPC45957
0.7191	Intermediate Similarity	NPC231599
0.7191	Intermediate Similarity	NPC475703
0.7191	Intermediate Similarity	NPC471657
0.7176	Intermediate Similarity	NPC223904
0.7176	Intermediate Similarity	NPC290508
0.7176	Intermediate Similarity	NPC293418
0.7176	Intermediate Similarity	NPC476625
0.7176	Intermediate Similarity	NPC302426
0.7176	Intermediate Similarity	NPC73052
0.7174	Intermediate Similarity	NPC135776
0.7159	Intermediate Similarity	NPC189311
0.7159	Intermediate Similarity	NPC284534
0.7159	Intermediate Similarity	NPC161957
0.7159	Intermediate Similarity	NPC323765
0.7159	Intermediate Similarity	NPC78089
0.7159	Intermediate Similarity	NPC204105
0.7159	Intermediate Similarity	NPC474369
0.7159	Intermediate Similarity	NPC300082
0.7158	Intermediate Similarity	NPC176845
0.7158	Intermediate Similarity	NPC471932
0.7143	Intermediate Similarity	NPC246173
0.7143	Intermediate Similarity	NPC306168
0.7143	Intermediate Similarity	NPC476627
0.7143	Intermediate Similarity	NPC312042
0.7143	Intermediate Similarity	NPC62815
0.7143	Intermediate Similarity	NPC472960
0.7143	Intermediate Similarity	NPC49946
0.7143	Intermediate Similarity	NPC169843
0.7128	Intermediate Similarity	NPC213078
0.7126	Intermediate Similarity	NPC65350
0.7126	Intermediate Similarity	NPC170377
0.7126	Intermediate Similarity	NPC22611
0.7126	Intermediate Similarity	NPC272814
0.7125	Intermediate Similarity	NPC67183
0.7111	Intermediate Similarity	NPC475906
0.7111	Intermediate Similarity	NPC469631
0.7111	Intermediate Similarity	NPC91248
0.7111	Intermediate Similarity	NPC469628
0.7111	Intermediate Similarity	NPC469653
0.7111	Intermediate Similarity	NPC471047
0.7108	Intermediate Similarity	NPC115719
0.7108	Intermediate Similarity	NPC141346
0.7108	Intermediate Similarity	NPC476317
0.7108	Intermediate Similarity	NPC473437
0.7108	Intermediate Similarity	NPC472959
0.7108	Intermediate Similarity	NPC142759
0.7108	Intermediate Similarity	NPC226242
0.7108	Intermediate Similarity	NPC25908
0.7108	Intermediate Similarity	NPC124289
0.7097	Intermediate Similarity	NPC127019
0.7093	Intermediate Similarity	NPC282293
0.7093	Intermediate Similarity	NPC42470
0.7093	Intermediate Similarity	NPC471325
0.7093	Intermediate Similarity	NPC141810
0.7079	Intermediate Similarity	NPC64153
0.7079	Intermediate Similarity	NPC195640
0.7079	Intermediate Similarity	NPC107787
0.7079	Intermediate Similarity	NPC472863
0.7079	Intermediate Similarity	NPC284902
0.7079	Intermediate Similarity	NPC220478
0.7079	Intermediate Similarity	NPC116575
0.7073	Intermediate Similarity	NPC469691
0.7073	Intermediate Similarity	NPC469643
0.7073	Intermediate Similarity	NPC143979
0.7073	Intermediate Similarity	NPC320537
0.7073	Intermediate Similarity	NPC469641
0.7073	Intermediate Similarity	NPC167049
0.7073	Intermediate Similarity	NPC476355
0.7073	Intermediate Similarity	NPC7382
0.7073	Intermediate Similarity	NPC474758
0.7065	Intermediate Similarity	NPC111114
0.7065	Intermediate Similarity	NPC45579
0.7065	Intermediate Similarity	NPC300312
0.7065	Intermediate Similarity	NPC261607
0.7065	Intermediate Similarity	NPC218301
0.7065	Intermediate Similarity	NPC472705
0.7059	Intermediate Similarity	NPC617
0.7059	Intermediate Similarity	NPC178277
0.7059	Intermediate Similarity	NPC150646
0.7059	Intermediate Similarity	NPC89128
0.7053	Intermediate Similarity	NPC161493
0.7051	Intermediate Similarity	NPC126899
0.7051	Intermediate Similarity	NPC304665
0.7051	Intermediate Similarity	NPC154728

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 NPC222210 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1688
0.2-0.3	4275
0.3-0.4	2045
0.4-0.5	584
0.5-0.6	229
0.6-0.7	142
0.7-0.8	19
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
0.764	Intermediate Similarity	NPD5693	Phase 1
0.7303	Intermediate Similarity	NPD5208	Approved
0.7222	Intermediate Similarity	NPD6904	Approved
0.7222	Intermediate Similarity	NPD6673	Approved
0.7222	Intermediate Similarity	NPD6080	Approved
0.7209	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.7143	Intermediate Similarity	NPD5207	Approved
0.7079	Intermediate Similarity	NPD6409	Approved
0.7079	Intermediate Similarity	NPD7334	Approved
0.7079	Intermediate Similarity	NPD5330	Approved
0.7079	Intermediate Similarity	NPD6098	Approved
0.7079	Intermediate Similarity	NPD6684	Approved
0.7079	Intermediate Similarity	NPD7521	Approved
0.7079	Intermediate Similarity	NPD7146	Approved
0.7065	Intermediate Similarity	NPD5694	Approved
0.7065	Intermediate Similarity	NPD6050	Approved
0.7033	Intermediate Similarity	NPD1695	Approved
0.6966	Remote Similarity	NPD1694	Approved
0.6932	Remote Similarity	NPD5362	Discontinued
0.6923	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6001	Approved
0.6842	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5695	Phase 3
0.6827	Remote Similarity	NPD6053	Discontinued
0.6818	Remote Similarity	NPD4221	Approved
0.6818	Remote Similarity	NPD4223	Phase 3
0.6818	Remote Similarity	NPD6435	Approved
0.6813	Remote Similarity	NPD3573	Approved
0.6778	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5785	Approved
0.6739	Remote Similarity	NPD5737	Approved
0.6739	Remote Similarity	NPD6672	Approved
0.6709	Remote Similarity	NPD7341	Phase 2
0.6709	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5786	Approved
0.6702	Remote Similarity	NPD5284	Approved
0.6702	Remote Similarity	NPD5281	Approved
0.6701	Remote Similarity	NPD6083	Phase 2
0.6701	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD5654	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD6051	Approved
0.6633	Remote Similarity	NPD5696	Approved
0.6625	Remote Similarity	NPD7331	Phase 2
0.6593	Remote Similarity	NPD5363	Approved
0.6593	Remote Similarity	NPD5329	Approved
0.6591	Remote Similarity	NPD5368	Approved
0.6588	Remote Similarity	NPD8039	Approved
0.6569	Remote Similarity	NPD6402	Approved
0.6569	Remote Similarity	NPD7128	Approved
0.6569	Remote Similarity	NPD6675	Approved
0.6569	Remote Similarity	NPD5739	Approved
0.6569	Remote Similarity	NPD6008	Approved
0.6531	Remote Similarity	NPD5959	Approved
0.6522	Remote Similarity	NPD4693	Phase 3
0.6522	Remote Similarity	NPD5690	Phase 2
0.6522	Remote Similarity	NPD4694	Approved
0.6522	Remote Similarity	NPD4689	Approved
0.6522	Remote Similarity	NPD4688	Approved
0.6522	Remote Similarity	NPD4138	Approved
0.6522	Remote Similarity	NPD4690	Approved
0.6522	Remote Similarity	NPD5280	Approved
0.6522	Remote Similarity	NPD5205	Approved
0.6517	Remote Similarity	NPD5369	Approved
0.6505	Remote Similarity	NPD5701	Approved
0.6505	Remote Similarity	NPD5697	Approved
0.6495	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD7638	Approved
0.6444	Remote Similarity	NPD4269	Approved
0.6444	Remote Similarity	NPD5209	Approved
0.6444	Remote Similarity	NPD4270	Approved
0.6442	Remote Similarity	NPD6881	Approved
0.6442	Remote Similarity	NPD6011	Approved
0.6442	Remote Similarity	NPD7320	Approved
0.6442	Remote Similarity	NPD6899	Approved
0.6421	Remote Similarity	NPD6698	Approved
0.6421	Remote Similarity	NPD46	Approved
0.6404	Remote Similarity	NPD4819	Approved
0.6404	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4820	Approved
0.6404	Remote Similarity	NPD4821	Approved
0.6404	Remote Similarity	NPD4822	Approved
0.64	Remote Similarity	NPD7640	Approved
0.64	Remote Similarity	NPD7639	Approved
0.6383	Remote Similarity	NPD4518	Approved
0.6381	Remote Similarity	NPD6373	Approved
0.6381	Remote Similarity	NPD6012	Approved
0.6381	Remote Similarity	NPD6372	Approved
0.6381	Remote Similarity	NPD6013	Approved
0.6381	Remote Similarity	NPD6014	Approved
0.6374	Remote Similarity	NPD5331	Approved
0.6374	Remote Similarity	NPD5332	Approved
0.6374	Remote Similarity	NPD7154	Phase 3
0.6373	Remote Similarity	NPD6052	Approved
0.6364	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4790	Discontinued
0.6321	Remote Similarity	NPD6883	Approved
0.6321	Remote Similarity	NPD7290	Approved
0.6321	Remote Similarity	NPD7102	Approved
0.6316	Remote Similarity	NPD4753	Phase 2
0.6304	Remote Similarity	NPD3666	Approved
0.6304	Remote Similarity	NPD3665	Phase 1
0.6304	Remote Similarity	NPD3133	Approved
0.6264	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD8130	Phase 1
0.6262	Remote Similarity	NPD6650	Approved
0.6262	Remote Similarity	NPD6847	Approved
0.6262	Remote Similarity	NPD6649	Approved
0.6262	Remote Similarity	NPD6869	Approved
0.6262	Remote Similarity	NPD6617	Approved
0.6262	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7507	Approved
0.625	Remote Similarity	NPD4096	Approved
0.6222	Remote Similarity	NPD4252	Approved
0.6207	Remote Similarity	NPD3702	Approved
0.6204	Remote Similarity	NPD6882	Approved
0.6204	Remote Similarity	NPD8297	Approved
0.62	Remote Similarity	NPD4755	Approved
0.619	Remote Similarity	NPD6614	Approved
0.618	Remote Similarity	NPD4271	Approved
0.618	Remote Similarity	NPD4268	Approved
0.6168	Remote Similarity	NPD6371	Approved
0.6154	Remote Similarity	NPD4692	Approved
0.6154	Remote Similarity	NPD4139	Approved
0.6146	Remote Similarity	NPD6101	Approved
0.6146	Remote Similarity	NPD5328	Approved
0.6146	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5778	Approved
0.6122	Remote Similarity	NPD6399	Phase 3
0.6122	Remote Similarity	NPD4202	Approved
0.6122	Remote Similarity	NPD5779	Approved
0.6118	Remote Similarity	NPD4747	Approved
0.6117	Remote Similarity	NPD5211	Phase 2
0.6111	Remote Similarity	NPD4195	Approved
0.6102	Remote Similarity	NPD7319	Approved
0.6078	Remote Similarity	NPD5285	Approved
0.6078	Remote Similarity	NPD5286	Approved
0.6078	Remote Similarity	NPD4700	Approved
0.6078	Remote Similarity	NPD4696	Approved
0.6047	Remote Similarity	NPD5276	Approved
0.6036	Remote Similarity	NPD6274	Approved
0.6022	Remote Similarity	NPD4788	Approved
0.602	Remote Similarity	NPD6079	Approved
0.602	Remote Similarity	NPD6411	Approved
0.6019	Remote Similarity	NPD5223	Approved
0.6	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD5279	Phase 3
0.6	Remote Similarity	NPD5210	Approved
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4519	Discontinued
0.6	Remote Similarity	NPD4137	Phase 3
0.6	Remote Similarity	NPD4629	Approved
0.6	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD4623	Approved
0.6	Remote Similarity	NPD3617	Approved
0.5982	Remote Similarity	NPD7115	Discovery
0.5982	Remote Similarity	NPD6317	Approved
0.5981	Remote Similarity	NPD6686	Approved
0.5962	Remote Similarity	NPD5225	Approved
0.5962	Remote Similarity	NPD4633	Approved
0.5962	Remote Similarity	NPD5226	Approved
0.5962	Remote Similarity	NPD7632	Discontinued
0.5962	Remote Similarity	NPD5224	Approved
0.596	Remote Similarity	NPD5133	Approved
0.5938	Remote Similarity	NPD4250	Approved
0.5938	Remote Similarity	NPD4251	Approved
0.593	Remote Similarity	NPD4691	Approved
0.5929	Remote Similarity	NPD6335	Approved
0.5929	Remote Similarity	NPD6313	Approved
0.5929	Remote Similarity	NPD6314	Approved
0.5922	Remote Similarity	NPD6404	Discontinued
0.5909	Remote Similarity	NPD4687	Approved
0.5909	Remote Similarity	NPD5733	Approved
0.5905	Remote Similarity	NPD5174	Approved
0.5905	Remote Similarity	NPD4754	Approved
0.5905	Remote Similarity	NPD5175	Approved
0.5877	Remote Similarity	NPD7100	Approved
0.5877	Remote Similarity	NPD7101	Approved
0.5841	Remote Similarity	NPD6009	Approved
0.5833	Remote Similarity	NPD6422	Discontinued
0.5833	Remote Similarity	NPD3618	Phase 1
0.5826	Remote Similarity	NPD6319	Approved
0.5825	Remote Similarity	NPD4225	Approved
0.5806	Remote Similarity	NPD857	Phase 3
0.5794	Remote Similarity	NPD4767	Approved
0.5794	Remote Similarity	NPD4768	Approved
0.5789	Remote Similarity	NPD4786	Approved
0.5784	Remote Similarity	NPD7839	Suspended
0.5784	Remote Similarity	NPD5222	Approved
0.5784	Remote Similarity	NPD4697	Phase 3
0.5784	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD5221	Approved
0.5776	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6908	Approved
0.5776	Remote Similarity	NPD6909	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