NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	424.26
Volume:	478.424
LogP:	4.96
LogD:	3.323
LogS:	-4.044
# Rotatable Bonds:	11
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.243
Synthetic Accessibility Score:	3.419
Fsp3:	0.407
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.014
MDCK Permeability:	1.919574788189493e-05
Pgp-inhibitor:	0.944
Pgp-substrate:	0.128
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.224

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	97.45433807373047%
Volume Distribution (VD):	1.175
Pgp-substrate:	0.7974182963371277%

ADMET: Metabolism

CYP1A2-inhibitor:	0.488
CYP1A2-substrate:	0.932
CYP2C19-inhibitor:	0.892
CYP2C19-substrate:	0.477
CYP2C9-inhibitor:	0.926
CYP2C9-substrate:	0.956
CYP2D6-inhibitor:	0.943
CYP2D6-substrate:	0.866
CYP3A4-inhibitor:	0.788
CYP3A4-substrate:	0.426

ADMET: Excretion

Clearance (CL):	6.887
Half-life (T1/2):	0.964

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.32
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.049
Maximum Recommended Daily Dose:	0.921
Skin Sensitization:	0.976
Carcinogencity:	0.605
Eye Corrosion:	0.886
Eye Irritation:	0.936
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC208223

Natural Product ID:	NPC208223
*Common Name:**	Dehydrozaluzanin C
IUPAC Name:	(3aS,6aR,9aR,9bS)-3,6,9-trimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2,8-dione
Synonyms:
Standard InCHIKey:	KNQLJJDOGQIMMT-IMIFBBOLSA-N
Standard InCHI:	InChI=1S/C15H16O3/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h10-11,13-14H,1-6H2/t10-,11-,13-,14-/m0/s1
SMILES:	C=C1C(=O)C[C@@H]2[C@H]1[C@H]1OC(=O)C(=C)[C@@H]1CCC2=C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2270297
PubChem CID:	10538257
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001770] Guaianolides and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214875]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18671	Saussurea involucrata	Species	Asteraceae	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	30

Activity Type	# Activity
Organism	30

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT855	Organism	Allium cepa	Allium cepa	Inhibition	>	40.0	%	PMID[528798]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Inhibition	>	40.0	%	PMID[528798]
NPT959	Organism	Solanum lycopersicum	Solanum lycopersicum	Inhibition	>	40.0	%	PMID[528798]
NPT3130	Organism	Lepidium sativum	Lepidium sativum	Inhibition	>	40.0	%	PMID[528798]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Inhibition	>	40.0	%	PMID[528798]
NPT855	Organism	Allium cepa	Allium cepa	Activity	>	40.0	%	PMID[528798]
NPT119	Organism	Triticum aestivum	Triticum aestivum	Activity	>	40.0	%	PMID[528798]
NPT959	Organism	Solanum lycopersicum	Solanum lycopersicum	Activity	>	40.0	%	PMID[528798]
NPT3130	Organism	Lepidium sativum	Lepidium sativum	Activity	>	40.0	%	PMID[528798]
NPT364	Organism	Lactuca sativa	Lactuca sativa	Activity	>	40.0	%	PMID[528798]

☑ 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 NPC208223 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	251
0.1-0.2	2167
0.2-0.3	9349
0.3-0.4	16391
0.4-0.5	8586
0.5-0.6	4582
0.6-0.7	1067
0.7-0.8	243
0.8-0.85	39
0.85-0.9	14
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9595	High Similarity	NPC293418
0.9595	High Similarity	NPC73052
0.9595	High Similarity	NPC290508
0.9577	High Similarity	NPC143979
0.9577	High Similarity	NPC320537
0.9221	High Similarity	NPC54468
0.9079	High Similarity	NPC6823
0.8875	High Similarity	NPC309757
0.8875	High Similarity	NPC236692
0.8875	High Similarity	NPC238593
0.8831	High Similarity	NPC74673
0.8831	High Similarity	NPC69271
0.8765	High Similarity	NPC118601
0.875	High Similarity	NPC5714
0.8734	High Similarity	NPC39588
0.8718	High Similarity	NPC10276
0.8718	High Similarity	NPC35089
0.8701	High Similarity	NPC182550
0.8659	High Similarity	NPC178875
0.8608	High Similarity	NPC246076
0.859	High Similarity	NPC276356
0.8554	High Similarity	NPC12872
0.8554	High Similarity	NPC168679
0.8537	High Similarity	NPC270270
0.8519	High Similarity	NPC161957
0.85	High Similarity	NPC245665
0.8395	Intermediate Similarity	NPC194859
0.8395	Intermediate Similarity	NPC224386
0.8354	Intermediate Similarity	NPC51507
0.8354	Intermediate Similarity	NPC302426
0.8353	Intermediate Similarity	NPC286341
0.8353	Intermediate Similarity	NPC191339
0.8313	Intermediate Similarity	NPC201658
0.8293	Intermediate Similarity	NPC284534
0.8293	Intermediate Similarity	NPC204105
0.8293	Intermediate Similarity	NPC300082
0.8272	Intermediate Similarity	NPC215294
0.8256	Intermediate Similarity	NPC153590
0.8256	Intermediate Similarity	NPC200237
0.825	Intermediate Similarity	NPC47635
0.8205	Intermediate Similarity	NPC65603
0.8193	Intermediate Similarity	NPC187661
0.8193	Intermediate Similarity	NPC304558
0.8193	Intermediate Similarity	NPC56593
0.8193	Intermediate Similarity	NPC64153
0.8182	Intermediate Similarity	NPC226669
0.8182	Intermediate Similarity	NPC193351
0.8182	Intermediate Similarity	NPC138408
0.8171	Intermediate Similarity	NPC156485
0.8125	Intermediate Similarity	NPC223904
0.8095	Intermediate Similarity	NPC190753
0.8095	Intermediate Similarity	NPC24728
0.8072	Intermediate Similarity	NPC235792
0.8072	Intermediate Similarity	NPC21471
0.8072	Intermediate Similarity	NPC33570
0.8068	Intermediate Similarity	NPC163228
0.8052	Intermediate Similarity	NPC469643
0.8052	Intermediate Similarity	NPC469641
0.8046	Intermediate Similarity	NPC473234
0.8046	Intermediate Similarity	NPC135776
0.8046	Intermediate Similarity	NPC60386
0.8046	Intermediate Similarity	NPC308656
0.8046	Intermediate Similarity	NPC473273
0.8046	Intermediate Similarity	NPC473263
0.8	Intermediate Similarity	NPC217983
0.8	Intermediate Similarity	NPC79549
0.8	Intermediate Similarity	NPC207114
0.8	Intermediate Similarity	NPC471149
0.7978	Intermediate Similarity	NPC91771
0.7978	Intermediate Similarity	NPC142529
0.7976	Intermediate Similarity	NPC470242
0.7976	Intermediate Similarity	NPC107787
0.7976	Intermediate Similarity	NPC67493
0.7975	Intermediate Similarity	NPC15975
0.7975	Intermediate Similarity	NPC195785
0.7975	Intermediate Similarity	NPC476794
0.7975	Intermediate Similarity	NPC470240
0.7955	Intermediate Similarity	NPC473331
0.7952	Intermediate Similarity	NPC115786
0.7949	Intermediate Similarity	NPC155587
0.7931	Intermediate Similarity	NPC74103
0.7931	Intermediate Similarity	NPC150978
0.7931	Intermediate Similarity	NPC70595
0.7931	Intermediate Similarity	NPC123177
0.7907	Intermediate Similarity	NPC472872
0.7907	Intermediate Similarity	NPC155935
0.7907	Intermediate Similarity	NPC215556
0.7907	Intermediate Similarity	NPC283409
0.7907	Intermediate Similarity	NPC38392
0.7875	Intermediate Similarity	NPC472960
0.7865	Intermediate Similarity	NPC476053
0.7857	Intermediate Similarity	NPC78089
0.7848	Intermediate Similarity	NPC235906
0.7816	Intermediate Similarity	NPC253144
0.7816	Intermediate Similarity	NPC19087
0.7816	Intermediate Similarity	NPC62815
0.7816	Intermediate Similarity	NPC216284
0.7816	Intermediate Similarity	NPC35809
0.7816	Intermediate Similarity	NPC297474
0.7816	Intermediate Similarity	NPC54065
0.7805	Intermediate Similarity	NPC126248
0.7805	Intermediate Similarity	NPC301477
0.7805	Intermediate Similarity	NPC25684
0.7805	Intermediate Similarity	NPC281949
0.7791	Intermediate Similarity	NPC224652
0.7791	Intermediate Similarity	NPC91248
0.7778	Intermediate Similarity	NPC63649
0.7778	Intermediate Similarity	NPC470239
0.7778	Intermediate Similarity	NPC264227
0.7778	Intermediate Similarity	NPC472965
0.7778	Intermediate Similarity	NPC469690
0.7778	Intermediate Similarity	NPC470244
0.7778	Intermediate Similarity	NPC469620
0.775	Intermediate Similarity	NPC103987
0.775	Intermediate Similarity	NPC53581
0.7727	Intermediate Similarity	NPC293001
0.7727	Intermediate Similarity	NPC63193
0.7727	Intermediate Similarity	NPC284185
0.7727	Intermediate Similarity	NPC184063
0.7727	Intermediate Similarity	NPC35959
0.7727	Intermediate Similarity	NPC171360
0.7727	Intermediate Similarity	NPC133888
0.7727	Intermediate Similarity	NPC57304
0.7727	Intermediate Similarity	NPC155215
0.7727	Intermediate Similarity	NPC29821
0.7722	Intermediate Similarity	NPC471491
0.7711	Intermediate Similarity	NPC173609
0.7703	Intermediate Similarity	NPC157518
0.7701	Intermediate Similarity	NPC32922
0.7701	Intermediate Similarity	NPC268298
0.7701	Intermediate Similarity	NPC4986
0.7692	Intermediate Similarity	NPC213947
0.7692	Intermediate Similarity	NPC108475
0.7692	Intermediate Similarity	NPC471150
0.7692	Intermediate Similarity	NPC170143
0.7683	Intermediate Similarity	NPC474981
0.7683	Intermediate Similarity	NPC258965
0.7683	Intermediate Similarity	NPC156658
0.7667	Intermediate Similarity	NPC275960
0.7667	Intermediate Similarity	NPC48803
0.7667	Intermediate Similarity	NPC193645
0.7667	Intermediate Similarity	NPC90121
0.7654	Intermediate Similarity	NPC299235
0.7647	Intermediate Similarity	NPC110405
0.764	Intermediate Similarity	NPC258216
0.7634	Intermediate Similarity	NPC171759
0.7625	Intermediate Similarity	NPC472959
0.7619	Intermediate Similarity	NPC128246
0.7619	Intermediate Similarity	NPC272814
0.7619	Intermediate Similarity	NPC194637
0.7614	Intermediate Similarity	NPC129419
0.7614	Intermediate Similarity	NPC301969
0.7614	Intermediate Similarity	NPC37607
0.759	Intermediate Similarity	NPC39411
0.759	Intermediate Similarity	NPC38642
0.759	Intermediate Similarity	NPC255580
0.7586	Intermediate Similarity	NPC53158
0.7564	Intermediate Similarity	NPC163003
0.7561	Intermediate Similarity	NPC617
0.7558	Intermediate Similarity	NPC284902
0.7532	Intermediate Similarity	NPC296522
0.7532	Intermediate Similarity	NPC144511
0.7531	Intermediate Similarity	NPC122264
0.7531	Intermediate Similarity	NPC187568
0.7531	Intermediate Similarity	NPC41780
0.7529	Intermediate Similarity	NPC138647
0.7529	Intermediate Similarity	NPC219011
0.7529	Intermediate Similarity	NPC470238
0.7528	Intermediate Similarity	NPC133698
0.7528	Intermediate Similarity	NPC261607
0.7528	Intermediate Similarity	NPC111114
0.7528	Intermediate Similarity	NPC475925
0.7528	Intermediate Similarity	NPC131209
0.7528	Intermediate Similarity	NPC300312
0.7527	Intermediate Similarity	NPC186861
0.7527	Intermediate Similarity	NPC471381
0.75	Intermediate Similarity	NPC311904
0.75	Intermediate Similarity	NPC226988
0.75	Intermediate Similarity	NPC288699
0.75	Intermediate Similarity	NPC169205
0.7473	Intermediate Similarity	NPC167893
0.7473	Intermediate Similarity	NPC472873
0.7473	Intermediate Similarity	NPC475900
0.7471	Intermediate Similarity	NPC186148
0.7471	Intermediate Similarity	NPC475703
0.7471	Intermediate Similarity	NPC237540
0.7468	Intermediate Similarity	NPC269206
0.7468	Intermediate Similarity	NPC58956
0.7468	Intermediate Similarity	NPC295633
0.7468	Intermediate Similarity	NPC472956
0.7444	Intermediate Similarity	NPC475700
0.7444	Intermediate Similarity	NPC472874
0.7442	Intermediate Similarity	NPC165162
0.7439	Intermediate Similarity	NPC128276
0.7436	Intermediate Similarity	NPC472955
0.7436	Intermediate Similarity	NPC18543
0.7419	Intermediate Similarity	NPC54843
0.7419	Intermediate Similarity	NPC141191
0.7416	Intermediate Similarity	NPC152467
0.7412	Intermediate Similarity	NPC318468

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 NPC208223 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	307
0.1-0.2	2911
0.2-0.3	3958
0.3-0.4	1400
0.4-0.5	415
0.5-0.6	138
0.6-0.7	19
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7701	Intermediate Similarity	NPD1695	Approved
0.7667	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD5785	Approved
0.6593	Remote Similarity	NPD5786	Approved
0.6569	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6435	Approved
0.6517	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5363	Approved
0.6452	Remote Similarity	NPD6903	Approved
0.6444	Remote Similarity	NPD5362	Discontinued
0.6413	Remote Similarity	NPD7521	Approved
0.6413	Remote Similarity	NPD6409	Approved
0.6413	Remote Similarity	NPD7146	Approved
0.6413	Remote Similarity	NPD5330	Approved
0.6413	Remote Similarity	NPD7334	Approved
0.6413	Remote Similarity	NPD6684	Approved
0.6404	Remote Similarity	NPD5369	Approved
0.6351	Remote Similarity	NPD9298	Approved
0.6333	Remote Similarity	NPD4270	Approved
0.6333	Remote Similarity	NPD4269	Approved
0.6311	Remote Similarity	NPD6008	Approved
0.6304	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5368	Approved
0.6277	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD6399	Phase 3
0.6154	Remote Similarity	NPD5209	Approved
0.6146	Remote Similarity	NPD5207	Approved
0.6111	Remote Similarity	NPD4252	Approved
0.6111	Remote Similarity	NPD6053	Discontinued
0.6105	Remote Similarity	NPD6672	Approved
0.6105	Remote Similarity	NPD5737	Approved
0.6087	Remote Similarity	NPD7154	Phase 3
0.6082	Remote Similarity	NPD5693	Phase 1
0.6075	Remote Similarity	NPD6371	Approved
0.6067	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4790	Discontinued
0.5976	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.596	Remote Similarity	NPD6001	Approved
0.5934	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD8034	Phase 2
0.5918	Remote Similarity	NPD8035	Phase 2
0.5914	Remote Similarity	NPD5331	Approved
0.5914	Remote Similarity	NPD5332	Approved
0.5909	Remote Similarity	NPD8039	Approved
0.5895	Remote Similarity	NPD4249	Approved
0.5882	Remote Similarity	NPD4225	Approved
0.5876	Remote Similarity	NPD6101	Approved
0.5876	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD5778	Approved
0.5859	Remote Similarity	NPD5779	Approved
0.5833	Remote Similarity	NPD3573	Approved
0.5833	Remote Similarity	NPD4250	Approved
0.5833	Remote Similarity	NPD4251	Approved
0.5816	Remote Similarity	NPD6698	Approved
0.5816	Remote Similarity	NPD46	Approved
0.5806	Remote Similarity	NPD3667	Approved
0.58	Remote Similarity	NPD5282	Discontinued
0.5794	Remote Similarity	NPD5697	Approved
0.5789	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5773	Remote Similarity	NPD5208	Approved
0.5761	Remote Similarity	NPD4821	Approved
0.5761	Remote Similarity	NPD4820	Approved
0.5761	Remote Similarity	NPD4822	Approved
0.5761	Remote Similarity	NPD4819	Approved
0.5758	Remote Similarity	NPD6079	Approved
0.5758	Remote Similarity	NPD6411	Approved
0.5752	Remote Similarity	NPD7115	Discovery
0.575	Remote Similarity	NPD3198	Approved
0.5747	Remote Similarity	NPD5777	Approved
0.5745	Remote Similarity	NPD4788	Approved
0.5743	Remote Similarity	NPD5695	Phase 3
0.5741	Remote Similarity	NPD6011	Approved
0.5741	Remote Similarity	NPD6899	Approved
0.5741	Remote Similarity	NPD7320	Approved
0.5741	Remote Similarity	NPD6881	Approved
0.5729	Remote Similarity	NPD3618	Phase 1
0.5729	Remote Similarity	NPD6098	Approved
0.5728	Remote Similarity	NPD7638	Approved
0.5728	Remote Similarity	NPD5696	Approved
0.5727	Remote Similarity	NPD6649	Approved
0.5727	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD6673	Approved
0.5714	Remote Similarity	NPD4271	Approved
0.5714	Remote Similarity	NPD5328	Approved
0.5714	Remote Similarity	NPD4268	Approved
0.5714	Remote Similarity	NPD6904	Approved
0.5714	Remote Similarity	NPD6080	Approved
0.5701	Remote Similarity	NPD6402	Approved
0.5701	Remote Similarity	NPD7128	Approved
0.5701	Remote Similarity	NPD6675	Approved
0.5701	Remote Similarity	NPD5739	Approved
0.5688	Remote Similarity	NPD6014	Approved
0.5688	Remote Similarity	NPD6373	Approved
0.5688	Remote Similarity	NPD6013	Approved
0.5688	Remote Similarity	NPD6372	Approved
0.5688	Remote Similarity	NPD6012	Approved
0.5684	Remote Similarity	NPD4786	Approved
0.5684	Remote Similarity	NPD3666	Approved
0.5684	Remote Similarity	NPD3665	Phase 1
0.5684	Remote Similarity	NPD3133	Approved
0.5684	Remote Similarity	NPD3668	Phase 3
0.5673	Remote Similarity	NPD7639	Approved
0.5673	Remote Similarity	NPD7640	Approved
0.5657	Remote Similarity	NPD5692	Phase 3
0.5648	Remote Similarity	NPD5701	Approved
0.5644	Remote Similarity	NPD7900	Approved
0.5644	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD7102	Approved
0.5636	Remote Similarity	NPD6883	Approved
0.5636	Remote Similarity	NPD7290	Approved
0.5631	Remote Similarity	NPD6083	Phase 2
0.5631	Remote Similarity	NPD6084	Phase 2
0.56	Remote Similarity	NPD7983	Approved
0.56	Remote Similarity	NPD5694	Approved
0.56	Remote Similarity	NPD6050	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