NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.1
Volume:	273.096
LogP:	0.619
LogD:	0.852
LogS:	-2.747
# Rotatable Bonds:	1
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.736
Synthetic Accessibility Score:	4.148
Fsp3:	0.4
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:	-5.044
MDCK Permeability:	4.255990461388137e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.772
Human Intestinal Absorption (HIA):	0.114
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.069

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.019
Plasma Protein Binding (PPB):	86.65618133544922%
Volume Distribution (VD):	0.952
Pgp-substrate:	12.811546325683594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.109
CYP1A2-substrate:	0.692
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.713
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.769
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.187
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	4.317
Half-life (T1/2):	0.629

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.351
Drug-inuced Liver Injury (DILI):	0.901
AMES Toxicity:	0.133
Rat Oral Acute Toxicity:	0.73
Maximum Recommended Daily Dose:	0.696
Skin Sensitization:	0.434
Carcinogencity:	0.538
Eye Corrosion:	0.003
Eye Irritation:	0.033
Respiratory Toxicity:	0.172

Download Data

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

Natural Product: NPC129419

Natural Product ID:	NPC129419
*Common Name:**	Lactucin
IUPAC Name:	(3aR,4R,9aS,9bR)-4-hydroxy-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
Synonyms:	Lactucin
Standard InCHIKey:	VJQAFLAZRVKAKM-QQUHWDOBSA-N
Standard InCHI:	InChI=1S/C15H16O5/c1-6-3-9(17)12-7(2)15(19)20-14(12)13-8(5-16)4-10(18)11(6)13/h4,9,12-14,16-17H,2-3,5H2,1H3/t9-,12-,13+,14+/m1/s1
SMILES:	OCC1=CC(=O)C2=C(C)C[C@H]([C@@H]3[C@@H]([C@@H]12)OC(=O)C3=C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521177
PubChem CID:	821383
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001245] Gamma butyrolactones

*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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]

☑ 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
ED50	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	260.0	umol/L	PMID[478278]
NPT4924	Organism	Haemonchus contortus	Haemonchus contortus	EC	=	2.89	mM	PMID[478279]

☑ 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 NPC129419 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	189
0.1-0.2	1128
0.2-0.3	4704
0.3-0.4	10026
0.4-0.5	14598
0.5-0.6	6775
0.6-0.7	3892
0.7-0.8	1141
0.8-0.85	172
0.85-0.9	63
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9881	High Similarity	NPC268298
0.9412	High Similarity	NPC237540
0.9405	High Similarity	NPC165162
0.907	High Similarity	NPC107787
0.9059	High Similarity	NPC115786
0.9059	High Similarity	NPC165287
0.8953	High Similarity	NPC78089
0.8851	High Similarity	NPC305475
0.8851	High Similarity	NPC475461
0.8837	High Similarity	NPC191476
0.8837	High Similarity	NPC141193
0.8837	High Similarity	NPC114979
0.8837	High Similarity	NPC96259
0.8824	High Similarity	NPC89555
0.8817	High Similarity	NPC141191
0.881	High Similarity	NPC302426
0.8778	High Similarity	NPC300312
0.8778	High Similarity	NPC261607
0.8778	High Similarity	NPC111114
0.875	High Similarity	NPC100487
0.8736	High Similarity	NPC255307
0.871	High Similarity	NPC169205
0.8706	High Similarity	NPC25684
0.8706	High Similarity	NPC281949
0.8706	High Similarity	NPC10276
0.8706	High Similarity	NPC35089
0.8706	High Similarity	NPC470241
0.8706	High Similarity	NPC301477
0.8696	High Similarity	NPC304886
0.8696	High Similarity	NPC193645
0.8696	High Similarity	NPC275960
0.8696	High Similarity	NPC48803
0.8696	High Similarity	NPC90121
0.869	High Similarity	NPC470244
0.869	High Similarity	NPC470239
0.8681	High Similarity	NPC135776
0.8605	High Similarity	NPC229825
0.8602	High Similarity	NPC185553
0.8587	High Similarity	NPC262133
0.8587	High Similarity	NPC167219
0.8587	High Similarity	NPC470010
0.8587	High Similarity	NPC470013
0.8587	High Similarity	NPC477131
0.8587	High Similarity	NPC323008
0.8571	High Similarity	NPC131209
0.8556	High Similarity	NPC295312
0.8506	High Similarity	NPC473390
0.8506	High Similarity	NPC131669
0.8506	High Similarity	NPC40746
0.8506	High Similarity	NPC169575
0.8495	Intermediate Similarity	NPC52044
0.8495	Intermediate Similarity	NPC170120
0.8488	Intermediate Similarity	NPC24417
0.8488	Intermediate Similarity	NPC255580
0.8488	Intermediate Similarity	NPC39411
0.8462	Intermediate Similarity	NPC106510
0.8462	Intermediate Similarity	NPC77337
0.8462	Intermediate Similarity	NPC71533
0.8452	Intermediate Similarity	NPC65603
0.8438	Intermediate Similarity	NPC150923
0.8427	Intermediate Similarity	NPC236692
0.8427	Intermediate Similarity	NPC150755
0.8427	Intermediate Similarity	NPC309757
0.8409	Intermediate Similarity	NPC156485
0.8409	Intermediate Similarity	NPC476804
0.8387	Intermediate Similarity	NPC198853
0.8372	Intermediate Similarity	NPC69271
0.8372	Intermediate Similarity	NPC74673
0.837	Intermediate Similarity	NPC133698
0.837	Intermediate Similarity	NPC475925
0.8353	Intermediate Similarity	NPC299235
0.8353	Intermediate Similarity	NPC108816
0.8353	Intermediate Similarity	NPC93763
0.8352	Intermediate Similarity	NPC32922
0.8352	Intermediate Similarity	NPC212664
0.8351	Intermediate Similarity	NPC86077
0.8316	Intermediate Similarity	NPC161493
0.8315	Intermediate Similarity	NPC470755
0.8298	Intermediate Similarity	NPC213698
0.8298	Intermediate Similarity	NPC67584
0.8295	Intermediate Similarity	NPC39588
0.8295	Intermediate Similarity	NPC59097
0.8283	Intermediate Similarity	NPC243998
0.828	Intermediate Similarity	NPC295204
0.828	Intermediate Similarity	NPC228451
0.828	Intermediate Similarity	NPC288240
0.828	Intermediate Similarity	NPC125674
0.828	Intermediate Similarity	NPC475912
0.828	Intermediate Similarity	NPC273579
0.828	Intermediate Similarity	NPC469645
0.828	Intermediate Similarity	NPC162205
0.828	Intermediate Similarity	NPC475302
0.828	Intermediate Similarity	NPC475838
0.828	Intermediate Similarity	NPC469692
0.8276	Intermediate Similarity	NPC52861
0.8261	Intermediate Similarity	NPC144133
0.8261	Intermediate Similarity	NPC179394
0.8261	Intermediate Similarity	NPC475855
0.8261	Intermediate Similarity	NPC469368
0.8256	Intermediate Similarity	NPC98557
0.8256	Intermediate Similarity	NPC167881
0.8256	Intermediate Similarity	NPC182550
0.8247	Intermediate Similarity	NPC128733
0.8247	Intermediate Similarity	NPC110443
0.8247	Intermediate Similarity	NPC185141
0.8247	Intermediate Similarity	NPC133907
0.8247	Intermediate Similarity	NPC46998
0.8242	Intermediate Similarity	NPC136879
0.8242	Intermediate Similarity	NPC476805
0.8235	Intermediate Similarity	NPC470240
0.8235	Intermediate Similarity	NPC195785
0.8235	Intermediate Similarity	NPC476794
0.8235	Intermediate Similarity	NPC15975
0.8235	Intermediate Similarity	NPC320630
0.8235	Intermediate Similarity	NPC7563
0.8235	Intermediate Similarity	NPC116177
0.8229	Intermediate Similarity	NPC221615
0.8214	Intermediate Similarity	NPC138408
0.8214	Intermediate Similarity	NPC226669
0.8214	Intermediate Similarity	NPC193351
0.8211	Intermediate Similarity	NPC213078
0.8202	Intermediate Similarity	NPC472957
0.8202	Intermediate Similarity	NPC158756
0.8202	Intermediate Similarity	NPC472958
0.8191	Intermediate Similarity	NPC469632
0.8191	Intermediate Similarity	NPC127019
0.8191	Intermediate Similarity	NPC121825
0.8191	Intermediate Similarity	NPC474247
0.8191	Intermediate Similarity	NPC474338
0.8182	Intermediate Similarity	NPC203659
0.8182	Intermediate Similarity	NPC173609
0.8172	Intermediate Similarity	NPC284185
0.8172	Intermediate Similarity	NPC70595
0.8172	Intermediate Similarity	NPC123177
0.8172	Intermediate Similarity	NPC150978
0.8172	Intermediate Similarity	NPC74103
0.8161	Intermediate Similarity	NPC223904
0.8161	Intermediate Similarity	NPC276356
0.8152	Intermediate Similarity	NPC12872
0.8152	Intermediate Similarity	NPC52198
0.8152	Intermediate Similarity	NPC218927
0.8152	Intermediate Similarity	NPC206001
0.8152	Intermediate Similarity	NPC117405
0.8152	Intermediate Similarity	NPC168679
0.814	Intermediate Similarity	NPC196653
0.814	Intermediate Similarity	NPC471465
0.8132	Intermediate Similarity	NPC160138
0.8132	Intermediate Similarity	NPC72513
0.8111	Intermediate Similarity	NPC161957
0.8105	Intermediate Similarity	NPC270013
0.8105	Intermediate Similarity	NPC14961
0.8105	Intermediate Similarity	NPC36954
0.81	Intermediate Similarity	NPC166115
0.81	Intermediate Similarity	NPC223450
0.8095	Intermediate Similarity	NPC476590
0.8095	Intermediate Similarity	NPC114727
0.809	Intermediate Similarity	NPC215294
0.8085	Intermediate Similarity	NPC81419
0.8085	Intermediate Similarity	NPC179746
0.8081	Intermediate Similarity	NPC110989
0.8068	Intermediate Similarity	NPC141810
0.8065	Intermediate Similarity	NPC37607
0.8065	Intermediate Similarity	NPC253144
0.8065	Intermediate Similarity	NPC301969
0.8061	Intermediate Similarity	NPC171759
0.8046	Intermediate Similarity	NPC63649
0.8046	Intermediate Similarity	NPC264227
0.8046	Intermediate Similarity	NPC270126
0.8046	Intermediate Similarity	NPC472965
0.8046	Intermediate Similarity	NPC89128
0.8043	Intermediate Similarity	NPC207114
0.8043	Intermediate Similarity	NPC202672
0.8043	Intermediate Similarity	NPC91248
0.8043	Intermediate Similarity	NPC473715
0.8043	Intermediate Similarity	NPC477302
0.8043	Intermediate Similarity	NPC476803
0.8043	Intermediate Similarity	NPC217983
0.8043	Intermediate Similarity	NPC475819
0.8041	Intermediate Similarity	NPC187268
0.8041	Intermediate Similarity	NPC473326
0.8022	Intermediate Similarity	NPC261721
0.8022	Intermediate Similarity	NPC67493
0.8022	Intermediate Similarity	NPC284902
0.8022	Intermediate Similarity	NPC469910
0.8022	Intermediate Similarity	NPC187661
0.8021	Intermediate Similarity	NPC279621
0.8021	Intermediate Similarity	NPC18019
0.8021	Intermediate Similarity	NPC24956
0.8021	Intermediate Similarity	NPC230800
0.8021	Intermediate Similarity	NPC476315
0.8	Intermediate Similarity	NPC303942
0.8	Intermediate Similarity	NPC309190
0.8	Intermediate Similarity	NPC57405
0.8	Intermediate Similarity	NPC96541
0.8	Intermediate Similarity	NPC474035
0.8	Intermediate Similarity	NPC81386
0.798	Intermediate Similarity	NPC303653
0.798	Intermediate Similarity	NPC140591
0.798	Intermediate Similarity	NPC291500
0.798	Intermediate Similarity	NPC189609

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 NPC129419 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1646
0.2-0.3	3704
0.3-0.4	2431
0.4-0.5	778
0.5-0.6	308
0.6-0.7	84
0.7-0.8	23
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8696	High Similarity	NPD1698	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD1695	Approved
0.7692	Intermediate Similarity	NPD7154	Phase 3
0.7684	Intermediate Similarity	NPD5785	Approved
0.767	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6371	Approved
0.7527	Intermediate Similarity	NPD5363	Approved
0.75	Intermediate Similarity	NPD5362	Discontinued
0.732	Intermediate Similarity	NPD46	Approved
0.732	Intermediate Similarity	NPD6698	Approved
0.7263	Intermediate Similarity	NPD5786	Approved
0.7204	Intermediate Similarity	NPD4269	Approved
0.7204	Intermediate Similarity	NPD6435	Approved
0.7204	Intermediate Similarity	NPD4270	Approved
0.7174	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD1694	Approved
0.7158	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD4225	Approved
0.7083	Intermediate Similarity	NPD4249	Approved
0.701	Intermediate Similarity	NPD4250	Approved
0.701	Intermediate Similarity	NPD4251	Approved
0.7	Intermediate Similarity	NPD6053	Discontinued
0.6989	Remote Similarity	NPD5368	Approved
0.6989	Remote Similarity	NPD4821	Approved
0.6989	Remote Similarity	NPD4819	Approved
0.6989	Remote Similarity	NPD4820	Approved
0.6989	Remote Similarity	NPD4822	Approved
0.6989	Remote Similarity	NPD4252	Approved
0.697	Remote Similarity	NPD7838	Discovery
0.6957	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4271	Approved
0.6957	Remote Similarity	NPD4268	Approved
0.6931	Remote Similarity	NPD5282	Discontinued
0.6915	Remote Similarity	NPD5369	Approved
0.69	Remote Similarity	NPD7983	Approved
0.6842	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5779	Approved
0.6832	Remote Similarity	NPD5778	Approved
0.6771	Remote Similarity	NPD5331	Approved
0.6771	Remote Similarity	NPD5332	Approved
0.6754	Remote Similarity	NPD7115	Discovery
0.6737	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6636	Remote Similarity	NPD6686	Approved
0.6607	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD7640	Approved
0.6604	Remote Similarity	NPD7639	Approved
0.6545	Remote Similarity	NPD5697	Approved
0.6535	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6101	Approved
0.6531	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD7638	Approved
0.6489	Remote Similarity	NPD4756	Discovery
0.6486	Remote Similarity	NPD6899	Approved
0.6486	Remote Similarity	NPD6881	Approved
0.6486	Remote Similarity	NPD7320	Approved
0.6476	Remote Similarity	NPD7839	Suspended
0.646	Remote Similarity	NPD6650	Approved
0.646	Remote Similarity	NPD6649	Approved
0.6455	Remote Similarity	NPD6675	Approved
0.6455	Remote Similarity	NPD7128	Approved
0.6455	Remote Similarity	NPD6402	Approved
0.6455	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD6012	Approved
0.6429	Remote Similarity	NPD6014	Approved
0.6429	Remote Similarity	NPD6013	Approved
0.6429	Remote Similarity	NPD6372	Approved
0.6429	Remote Similarity	NPD6373	Approved
0.6415	Remote Similarity	NPD6084	Phase 2
0.6415	Remote Similarity	NPD6083	Phase 2
0.6408	Remote Similarity	NPD6411	Approved
0.6396	Remote Similarity	NPD5701	Approved
0.6389	Remote Similarity	NPD5344	Discontinued
0.6381	Remote Similarity	NPD5695	Phase 3
0.6373	Remote Similarity	NPD5370	Suspended
0.6372	Remote Similarity	NPD7290	Approved
0.6372	Remote Similarity	NPD7102	Approved
0.6372	Remote Similarity	NPD6883	Approved
0.6364	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5696	Approved
0.6339	Remote Similarity	NPD6011	Approved
0.633	Remote Similarity	NPD5211	Phase 2
0.6316	Remote Similarity	NPD6617	Approved
0.6316	Remote Similarity	NPD8130	Phase 1
0.6316	Remote Similarity	NPD6847	Approved
0.6316	Remote Similarity	NPD6869	Approved
0.6306	Remote Similarity	NPD6008	Approved
0.6275	Remote Similarity	NPD6903	Approved
0.6262	Remote Similarity	NPD7902	Approved
0.6261	Remote Similarity	NPD6882	Approved
0.6261	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD6684	Approved
0.6238	Remote Similarity	NPD7521	Approved
0.6238	Remote Similarity	NPD7334	Approved
0.6238	Remote Similarity	NPD7146	Approved
0.6238	Remote Similarity	NPD6409	Approved
0.6238	Remote Similarity	NPD5330	Approved
0.6238	Remote Similarity	NPD3618	Phase 1
0.6216	Remote Similarity	NPD5141	Approved
0.62	Remote Similarity	NPD3665	Phase 1
0.62	Remote Similarity	NPD3666	Approved
0.62	Remote Similarity	NPD3133	Approved
0.6162	Remote Similarity	NPD3667	Approved
0.6147	Remote Similarity	NPD5286	Approved
0.6147	Remote Similarity	NPD6648	Approved
0.6147	Remote Similarity	NPD4696	Approved
0.6147	Remote Similarity	NPD5285	Approved
0.6139	Remote Similarity	NPD1696	Phase 3
0.6132	Remote Similarity	NPD7748	Approved
0.6126	Remote Similarity	NPD6647	Phase 2
0.6117	Remote Similarity	NPD6672	Approved
0.6117	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5737	Approved
0.6116	Remote Similarity	NPD8515	Approved
0.6116	Remote Similarity	NPD8517	Approved
0.6116	Remote Similarity	NPD8516	Approved
0.6116	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6116	Remote Similarity	NPD8513	Phase 3
0.6111	Remote Similarity	NPD7331	Phase 2
0.6111	Remote Similarity	NPD4755	Approved
0.6105	Remote Similarity	NPD8039	Approved
0.6102	Remote Similarity	NPD6274	Approved
0.6095	Remote Similarity	NPD5284	Approved
0.6095	Remote Similarity	NPD5693	Phase 1
0.6095	Remote Similarity	NPD6079	Approved
0.6095	Remote Similarity	NPD5281	Approved
0.6095	Remote Similarity	NPD7515	Phase 2
0.6078	Remote Similarity	NPD5279	Phase 3
0.6075	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD4629	Approved
0.6075	Remote Similarity	NPD5210	Approved
0.6058	Remote Similarity	NPD4753	Phase 2
0.6058	Remote Similarity	NPD5328	Approved
0.6048	Remote Similarity	NPD7507	Approved
0.604	Remote Similarity	NPD4786	Approved
0.6036	Remote Similarity	NPD5224	Approved
0.6036	Remote Similarity	NPD5226	Approved
0.6036	Remote Similarity	NPD4633	Approved
0.6036	Remote Similarity	NPD7632	Discontinued
0.6036	Remote Similarity	NPD5225	Approved
0.6034	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5222	Approved
0.6019	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5221	Approved
0.6019	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD7341	Phase 2
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5207	Approved
0.6	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4700	Approved
0.5982	Remote Similarity	NPD5175	Approved
0.5982	Remote Similarity	NPD5174	Approved
0.5981	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD7900	Approved
0.5968	Remote Similarity	NPD7492	Approved
0.5965	Remote Similarity	NPD6412	Phase 2
0.5963	Remote Similarity	NPD5173	Approved
0.596	Remote Similarity	NPD4695	Discontinued
0.595	Remote Similarity	NPD7101	Approved
0.595	Remote Similarity	NPD7100	Approved
0.5948	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5223	Approved
0.5941	Remote Similarity	NPD6110	Phase 1
0.5938	Remote Similarity	NPD7260	Phase 2
0.5932	Remote Similarity	NPD4632	Approved
0.5922	Remote Similarity	NPD4623	Approved
0.5922	Remote Similarity	NPD4519	Discontinued
0.5922	Remote Similarity	NPD6422	Discontinued
0.592	Remote Similarity	NPD6616	Approved
0.5917	Remote Similarity	NPD6317	Approved
0.5906	Remote Similarity	NPD7319	Approved
0.5902	Remote Similarity	NPD6054	Approved
0.5902	Remote Similarity	NPD6319	Approved
0.5897	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5891	Remote Similarity	NPD6845	Suspended
0.5888	Remote Similarity	NPD4202	Approved
0.5887	Remote Similarity	NPD7642	Approved
0.5882	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7078	Approved
0.5873	Remote Similarity	NPD8074	Phase 3
0.587	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD7641	Discontinued
0.5868	Remote Similarity	NPD6314	Approved
0.5868	Remote Similarity	NPD6313	Approved
0.5868	Remote Similarity	NPD6335	Approved
0.5854	Remote Similarity	NPD6015	Approved
0.5854	Remote Similarity	NPD6016	Approved
0.5833	Remote Similarity	NPD6868	Approved
0.5833	Remote Similarity	NPD6001	Approved
0.5827	Remote Similarity	NPD7736	Approved
0.5812	Remote Similarity	NPD6420	Discontinued
0.5806	Remote Similarity	NPD6370	Approved
0.5806	Remote Similarity	NPD5988	Approved
0.5794	Remote Similarity	NPD8034	Phase 2
0.5794	Remote Similarity	NPD8035	Phase 2

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