NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.15
Volume:	272.215
LogP:	2.265
LogD:	2.035
LogS:	-3.373
# Rotatable Bonds:	0
TPSA:	73.83
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.67
Synthetic Accessibility Score:	4.655
Fsp3:	0.733
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:	-4.639
MDCK Permeability:	1.2386236448946875e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.087
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.004

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.331
Plasma Protein Binding (PPB):	93.43181610107422%
Volume Distribution (VD):	1.335
Pgp-substrate:	8.574695587158203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.505
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.703
CYP2C9-inhibitor:	0.049
CYP2C9-substrate:	0.655
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.363
CYP3A4-inhibitor:	0.023
CYP3A4-substrate:	0.204

ADMET: Excretion

Clearance (CL):	8.58
Half-life (T1/2):	0.649

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.689
Drug-inuced Liver Injury (DILI):	0.876
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.067
Maximum Recommended Daily Dose:	0.031
Skin Sensitization:	0.32
Carcinogencity:	0.542
Eye Corrosion:	0.009
Eye Irritation:	0.047
Respiratory Toxicity:	0.157

Download Data

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

Natural Product: NPC53011

Natural Product ID:	NPC53011
*Common Name:**	Phaeocaulisin B
IUPAC Name:	(3aR,5R,5aS,8R,8aR)-5,8-dihydroxy-1,5,8-trimethyl-4,5a,6,7,8a,9-hexahydro-3aH-azuleno[6,5-b]furan-2-one
Synonyms:
Standard InCHIKey:	BQDXDGDOYPUUOD-PGKPSXLWSA-N
Standard InCHI:	InChI=1S/C15H22O4/c1-8-9-6-11-10(4-5-14(11,2)17)15(3,18)7-12(9)19-13(8)16/h10-12,17-18H,4-7H2,1-3H3/t10-,11+,12+,14+,15+/m0/s1
SMILES:	O=C1O[C@H]2C(=C1C)C[C@@H]1[C@@H]([C@](C2)(C)O)CC[C@@]1(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386501
PubChem CID:	71725703
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
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23755850]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	Radix	n.a.	n.a.	PMID[29236488]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25209	Curcuma aromatica	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18068	Curcuma phaeocaulis	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
IC50	1
Others	3

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1900.0	nM	PMID[503796]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	72.04	%	PMID[503797]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	67.54	%	PMID[503797]
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	76.41	%	PMID[503797]

☑ 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 NPC53011 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	213
0.1-0.2	1698
0.2-0.3	6407
0.3-0.4	16121
0.4-0.5	9289
0.5-0.6	6257
0.6-0.7	2414
0.7-0.8	262
0.8-0.85	30
0.85-0.9	1
0.9-0.95	1
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC154893
1.0	High Similarity	NPC37005
1.0	High Similarity	NPC16887
0.9259	High Similarity	NPC290052
0.8764	High Similarity	NPC98165
0.8652	High Similarity	NPC37408
0.8488	Intermediate Similarity	NPC191283
0.8471	Intermediate Similarity	NPC287015
0.8471	Intermediate Similarity	NPC146850
0.8444	Intermediate Similarity	NPC220221
0.8444	Intermediate Similarity	NPC469873
0.8276	Intermediate Similarity	NPC45957
0.8276	Intermediate Similarity	NPC471657
0.8261	Intermediate Similarity	NPC477949
0.8256	Intermediate Similarity	NPC245434
0.8242	Intermediate Similarity	NPC52044
0.8242	Intermediate Similarity	NPC67584
0.8222	Intermediate Similarity	NPC272293
0.8222	Intermediate Similarity	NPC40821
0.8222	Intermediate Similarity	NPC32862
0.8202	Intermediate Similarity	NPC471184
0.8182	Intermediate Similarity	NPC79549
0.8152	Intermediate Similarity	NPC213078
0.8132	Intermediate Similarity	NPC477131
0.8132	Intermediate Similarity	NPC127019
0.8132	Intermediate Similarity	NPC470013
0.8132	Intermediate Similarity	NPC470010
0.8132	Intermediate Similarity	NPC323008
0.8132	Intermediate Similarity	NPC262133
0.809	Intermediate Similarity	NPC32922
0.809	Intermediate Similarity	NPC212664
0.809	Intermediate Similarity	NPC215556
0.8065	Intermediate Similarity	NPC161493
0.8046	Intermediate Similarity	NPC471185
0.8043	Intermediate Similarity	NPC170120
0.8043	Intermediate Similarity	NPC213698
0.8043	Intermediate Similarity	NPC329435
0.8	Intermediate Similarity	NPC301969
0.8	Intermediate Similarity	NPC37607
0.8	Intermediate Similarity	NPC216284
0.7979	Intermediate Similarity	NPC221615
0.7935	Intermediate Similarity	NPC198853
0.7912	Intermediate Similarity	NPC155215
0.7912	Intermediate Similarity	NPC131209
0.7912	Intermediate Similarity	NPC133698
0.7912	Intermediate Similarity	NPC475925
0.7841	Intermediate Similarity	NPC284534
0.7841	Intermediate Similarity	NPC204105
0.7841	Intermediate Similarity	NPC300082
0.7826	Intermediate Similarity	NPC258216
0.7826	Intermediate Similarity	NPC135776
0.7812	Intermediate Similarity	NPC477950
0.7812	Intermediate Similarity	NPC150923
0.7778	Intermediate Similarity	NPC91248
0.7766	Intermediate Similarity	NPC24956
0.7766	Intermediate Similarity	NPC18019
0.7753	Intermediate Similarity	NPC67493
0.7742	Intermediate Similarity	NPC281775
0.7742	Intermediate Similarity	NPC96541
0.7692	Intermediate Similarity	NPC155935
0.766	Intermediate Similarity	NPC472873
0.766	Intermediate Similarity	NPC304886
0.766	Intermediate Similarity	NPC163228
0.7647	Intermediate Similarity	NPC23187
0.7614	Intermediate Similarity	NPC111409
0.7614	Intermediate Similarity	NPC245665
0.7609	Intermediate Similarity	NPC297474
0.7609	Intermediate Similarity	NPC54065
0.7609	Intermediate Similarity	NPC35809
0.7586	Intermediate Similarity	NPC59994
0.7586	Intermediate Similarity	NPC78677
0.7582	Intermediate Similarity	NPC217983
0.7582	Intermediate Similarity	NPC207114
0.7582	Intermediate Similarity	NPC178875
0.7582	Intermediate Similarity	NPC224652
0.7558	Intermediate Similarity	NPC226226
0.7558	Intermediate Similarity	NPC55304
0.7556	Intermediate Similarity	NPC187661
0.7556	Intermediate Similarity	NPC64153
0.7556	Intermediate Similarity	NPC137253
0.7551	Intermediate Similarity	NPC86077
0.7529	Intermediate Similarity	NPC476439
0.7528	Intermediate Similarity	NPC32223
0.7528	Intermediate Similarity	NPC156485
0.7527	Intermediate Similarity	NPC171360
0.7527	Intermediate Similarity	NPC184063
0.7527	Intermediate Similarity	NPC249034
0.7527	Intermediate Similarity	NPC63193
0.7527	Intermediate Similarity	NPC57304
0.7527	Intermediate Similarity	NPC293001
0.7527	Intermediate Similarity	NPC133888
0.7527	Intermediate Similarity	NPC29821
0.7527	Intermediate Similarity	NPC35959
0.7526	Intermediate Similarity	NPC70865
0.75	Intermediate Similarity	NPC4986
0.75	Intermediate Similarity	NPC213947
0.75	Intermediate Similarity	NPC472872
0.75	Intermediate Similarity	NPC220217
0.75	Intermediate Similarity	NPC108475
0.75	Intermediate Similarity	NPC243998
0.75	Intermediate Similarity	NPC223450
0.75	Intermediate Similarity	NPC170143
0.75	Intermediate Similarity	NPC54737
0.75	Intermediate Similarity	NPC119855
0.7475	Intermediate Similarity	NPC10232
0.7475	Intermediate Similarity	NPC196471
0.7475	Intermediate Similarity	NPC97487
0.7475	Intermediate Similarity	NPC472821
0.7475	Intermediate Similarity	NPC189588
0.7475	Intermediate Similarity	NPC160583
0.7475	Intermediate Similarity	NPC124881
0.7475	Intermediate Similarity	NPC187302
0.7474	Intermediate Similarity	NPC476053
0.7473	Intermediate Similarity	NPC471796
0.7473	Intermediate Similarity	NPC118601
0.7471	Intermediate Similarity	NPC156658
0.7471	Intermediate Similarity	NPC258965
0.7449	Intermediate Similarity	NPC171759
0.7449	Intermediate Similarity	NPC25177
0.7449	Intermediate Similarity	NPC222875
0.7449	Intermediate Similarity	NPC247701
0.7449	Intermediate Similarity	NPC268829
0.7449	Intermediate Similarity	NPC475099
0.7449	Intermediate Similarity	NPC295110
0.7447	Intermediate Similarity	NPC110022
0.7447	Intermediate Similarity	NPC471483
0.7444	Intermediate Similarity	NPC235792
0.7426	Intermediate Similarity	NPC26617
0.7423	Intermediate Similarity	NPC45125
0.7419	Intermediate Similarity	NPC209816
0.7419	Intermediate Similarity	NPC473448
0.7419	Intermediate Similarity	NPC19087
0.7416	Intermediate Similarity	NPC471340
0.7416	Intermediate Similarity	NPC128246
0.7416	Intermediate Similarity	NPC321385
0.7412	Intermediate Similarity	NPC476317
0.7396	Intermediate Similarity	NPC113433
0.7396	Intermediate Similarity	NPC319861
0.7396	Intermediate Similarity	NPC320231
0.7379	Intermediate Similarity	NPC15551
0.7374	Intermediate Similarity	NPC470972
0.7368	Intermediate Similarity	NPC472467
0.7368	Intermediate Similarity	NPC90453
0.7363	Intermediate Similarity	NPC56593
0.7363	Intermediate Similarity	NPC477668
0.7347	Intermediate Similarity	NPC280963
0.7347	Intermediate Similarity	NPC471381
0.7347	Intermediate Similarity	NPC130792
0.7347	Intermediate Similarity	NPC186861
0.734	Intermediate Similarity	NPC78594
0.734	Intermediate Similarity	NPC290651
0.734	Intermediate Similarity	NPC158061
0.734	Intermediate Similarity	NPC221282
0.7333	Intermediate Similarity	NPC224386
0.7333	Intermediate Similarity	NPC194859
0.7327	Intermediate Similarity	NPC166115
0.7327	Intermediate Similarity	NPC470980
0.732	Intermediate Similarity	NPC181151
0.732	Intermediate Similarity	NPC471150
0.732	Intermediate Similarity	NPC311904
0.7312	Intermediate Similarity	NPC38392
0.7308	Intermediate Similarity	NPC71680
0.7303	Intermediate Similarity	NPC246076
0.7294	Intermediate Similarity	NPC329852
0.7292	Intermediate Similarity	NPC224689
0.7292	Intermediate Similarity	NPC471915
0.7292	Intermediate Similarity	NPC111273
0.7283	Intermediate Similarity	NPC270270
0.7283	Intermediate Similarity	NPC24728
0.7283	Intermediate Similarity	NPC160138
0.7282	Intermediate Similarity	NPC59489
0.7282	Intermediate Similarity	NPC139838
0.7273	Intermediate Similarity	NPC80622
0.7263	Intermediate Similarity	NPC473273
0.7263	Intermediate Similarity	NPC308656
0.7263	Intermediate Similarity	NPC153590
0.7263	Intermediate Similarity	NPC473234
0.7263	Intermediate Similarity	NPC60386
0.7263	Intermediate Similarity	NPC473263
0.7263	Intermediate Similarity	NPC472641
0.7263	Intermediate Similarity	NPC472640
0.7238	Intermediate Similarity	NPC241477
0.7234	Intermediate Similarity	NPC472642
0.7234	Intermediate Similarity	NPC312042
0.7228	Intermediate Similarity	NPC472822
0.7228	Intermediate Similarity	NPC200861
0.7222	Intermediate Similarity	NPC231601
0.7222	Intermediate Similarity	NPC472473
0.7216	Intermediate Similarity	NPC126156
0.7216	Intermediate Similarity	NPC475304
0.7216	Intermediate Similarity	NPC91771
0.7216	Intermediate Similarity	NPC142529
0.7212	Intermediate Similarity	NPC48305
0.7212	Intermediate Similarity	NPC474923
0.7209	Intermediate Similarity	NPC469880
0.7204	Intermediate Similarity	NPC471149
0.7191	Intermediate Similarity	NPC471661
0.7191	Intermediate Similarity	NPC126248
0.7188	Intermediate Similarity	NPC474338
0.7174	Intermediate Similarity	NPC261253

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 NPC53011 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	2419
0.2-0.3	3974
0.3-0.4	1853
0.4-0.5	394
0.5-0.6	235
0.6-0.7	45
0.7-0.8	4
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
0.75	Intermediate Similarity	NPD1695	Approved
0.7444	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD6053	Discontinued
0.7174	Intermediate Similarity	NPD4249	Approved
0.7097	Intermediate Similarity	NPD4250	Approved
0.7097	Intermediate Similarity	NPD4251	Approved
0.7048	Intermediate Similarity	NPD6371	Approved
0.69	Remote Similarity	NPD7638	Approved
0.6889	Remote Similarity	NPD4819	Approved
0.6889	Remote Similarity	NPD4822	Approved
0.6889	Remote Similarity	NPD4821	Approved
0.6889	Remote Similarity	NPD4820	Approved
0.6889	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7838	Discovery
0.6848	Remote Similarity	NPD5362	Discontinued
0.6832	Remote Similarity	NPD7640	Approved
0.6832	Remote Similarity	NPD7639	Approved
0.6768	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7327	Approved
0.6757	Remote Similarity	NPD7328	Approved
0.6701	Remote Similarity	NPD6698	Approved
0.6701	Remote Similarity	NPD46	Approved
0.6699	Remote Similarity	NPD7632	Discontinued
0.6696	Remote Similarity	NPD7516	Approved
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD4268	Approved
0.6637	Remote Similarity	NPD8377	Approved
0.6637	Remote Similarity	NPD8294	Approved
0.663	Remote Similarity	NPD4790	Discontinued
0.6579	Remote Similarity	NPD8033	Approved
0.6579	Remote Similarity	NPD8380	Approved
0.6579	Remote Similarity	NPD8335	Approved
0.6579	Remote Similarity	NPD8379	Approved
0.6579	Remote Similarity	NPD8378	Approved
0.6579	Remote Similarity	NPD8296	Approved
0.6559	Remote Similarity	NPD6435	Approved
0.6531	Remote Similarity	NPD5785	Approved
0.6496	Remote Similarity	NPD7507	Approved
0.6481	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5344	Discontinued
0.6436	Remote Similarity	NPD5695	Phase 3
0.6429	Remote Similarity	NPD6051	Approved
0.6429	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6686	Approved
0.6354	Remote Similarity	NPD5363	Approved
0.6346	Remote Similarity	NPD6648	Approved
0.6344	Remote Similarity	NPD5368	Approved
0.6333	Remote Similarity	NPD7319	Approved
0.6316	Remote Similarity	NPD7154	Phase 3
0.6311	Remote Similarity	NPD6084	Phase 2
0.6311	Remote Similarity	NPD6083	Phase 2
0.63	Remote Similarity	NPD7637	Suspended
0.6293	Remote Similarity	NPD7503	Approved
0.6277	Remote Similarity	NPD5369	Approved
0.625	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.625	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7320	Approved
0.6211	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD4269	Approved
0.6211	Remote Similarity	NPD4270	Approved
0.6204	Remote Similarity	NPD6008	Approved
0.6204	Remote Similarity	NPD7128	Approved
0.6204	Remote Similarity	NPD6402	Approved
0.6204	Remote Similarity	NPD6675	Approved
0.6204	Remote Similarity	NPD5739	Approved
0.6186	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5282	Discontinued
0.6147	Remote Similarity	NPD5701	Approved
0.6147	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5697	Approved
0.6146	Remote Similarity	NPD6695	Phase 3
0.6139	Remote Similarity	NPD5693	Phase 1
0.6129	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD5786	Approved
0.6095	Remote Similarity	NPD4225	Approved
0.6091	Remote Similarity	NPD6881	Approved
0.6091	Remote Similarity	NPD6899	Approved
0.6082	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD5209	Approved
0.6036	Remote Similarity	NPD6012	Approved
0.6036	Remote Similarity	NPD6014	Approved
0.6036	Remote Similarity	NPD6372	Approved
0.6036	Remote Similarity	NPD6013	Approved
0.6036	Remote Similarity	NPD6373	Approved
0.602	Remote Similarity	NPD1694	Approved
0.6	Remote Similarity	NPD6412	Phase 2
0.6	Remote Similarity	NPD4252	Approved
0.6	Remote Similarity	NPD6903	Approved
0.5982	Remote Similarity	NPD7290	Approved
0.5982	Remote Similarity	NPD6883	Approved
0.5982	Remote Similarity	NPD7102	Approved
0.598	Remote Similarity	NPD5284	Approved
0.598	Remote Similarity	NPD7983	Approved
0.598	Remote Similarity	NPD5281	Approved
0.5965	Remote Similarity	NPD4632	Approved
0.596	Remote Similarity	NPD7334	Approved
0.596	Remote Similarity	NPD5330	Approved
0.596	Remote Similarity	NPD6409	Approved
0.596	Remote Similarity	NPD7146	Approved
0.596	Remote Similarity	NPD6684	Approved
0.596	Remote Similarity	NPD7521	Approved
0.5946	Remote Similarity	NPD6011	Approved
0.5941	Remote Similarity	NPD4753	Phase 2
0.5932	Remote Similarity	NPD6319	Approved
0.5929	Remote Similarity	NPD6847	Approved
0.5929	Remote Similarity	NPD8130	Phase 1
0.5929	Remote Similarity	NPD6649	Approved
0.5929	Remote Similarity	NPD6617	Approved
0.5929	Remote Similarity	NPD6869	Approved
0.5929	Remote Similarity	NPD6650	Approved
0.5922	Remote Similarity	NPD5778	Approved
0.5922	Remote Similarity	NPD6399	Phase 3
0.5922	Remote Similarity	NPD5779	Approved
0.59	Remote Similarity	NPD7524	Approved
0.59	Remote Similarity	NPD7750	Discontinued
0.5877	Remote Similarity	NPD8297	Approved
0.5877	Remote Similarity	NPD6882	Approved
0.5868	Remote Similarity	NPD7492	Approved
0.5856	Remote Similarity	NPD6685	Approved
0.5849	Remote Similarity	NPD4755	Approved
0.5842	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6931	Approved
0.5833	Remote Similarity	NPD6930	Phase 2
0.582	Remote Similarity	NPD6616	Approved
0.5812	Remote Similarity	NPD6009	Approved
0.5812	Remote Similarity	NPD7115	Discovery
0.581	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD6059	Approved
0.5798	Remote Similarity	NPD6054	Approved
0.5789	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD6080	Approved
0.5784	Remote Similarity	NPD6673	Approved
0.5784	Remote Similarity	NPD6904	Approved
0.578	Remote Similarity	NPD5211	Phase 2
0.5772	Remote Similarity	NPD8293	Discontinued
0.5772	Remote Similarity	NPD7078	Approved
0.5769	Remote Similarity	NPD4202	Approved
0.5758	Remote Similarity	NPD3665	Phase 1
0.5758	Remote Similarity	NPD3666	Approved
0.5758	Remote Similarity	NPD3133	Approved
0.5755	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.575	Remote Similarity	NPD5983	Phase 2
0.575	Remote Similarity	NPD6016	Approved
0.575	Remote Similarity	NPD6015	Approved
0.5743	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5286	Approved
0.5741	Remote Similarity	NPD4700	Approved
0.5741	Remote Similarity	NPD4696	Approved
0.5741	Remote Similarity	NPD5285	Approved
0.5729	Remote Similarity	NPD6929	Approved
0.5729	Remote Similarity	NPD4195	Approved
0.5728	Remote Similarity	NPD5692	Phase 3
0.5728	Remote Similarity	NPD5207	Approved
0.5726	Remote Similarity	NPD7736	Approved
0.5726	Remote Similarity	NPD6274	Approved
0.5714	Remote Similarity	NPD4221	Approved
0.5714	Remote Similarity	NPD4223	Phase 3
0.5702	Remote Similarity	NPD5988	Approved
0.5702	Remote Similarity	NPD6370	Approved
0.569	Remote Similarity	NPD8133	Approved
0.5686	Remote Similarity	NPD5737	Approved
0.5686	Remote Similarity	NPD6672	Approved
0.5686	Remote Similarity	NPD5208	Approved
0.5676	Remote Similarity	NPD5141	Approved
0.5673	Remote Similarity	NPD7087	Discontinued
0.5673	Remote Similarity	NPD6050	Approved
0.5673	Remote Similarity	NPD5694	Approved
0.567	Remote Similarity	NPD7514	Phase 3
0.566	Remote Similarity	NPD4629	Approved
0.566	Remote Similarity	NPD5210	Approved
0.5656	Remote Similarity	NPD7604	Phase 2
0.5647	Remote Similarity	NPD3198	Approved
0.5636	Remote Similarity	NPD5226	Approved
0.5636	Remote Similarity	NPD5224	Approved
0.5636	Remote Similarity	NPD5225	Approved
0.5636	Remote Similarity	NPD4633	Approved
0.5625	Remote Similarity	NPD4211	Phase 1
0.5625	Remote Similarity	NPD4238	Approved
0.5625	Remote Similarity	NPD4802	Phase 2
0.56	Remote Similarity	NPD4197	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