NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	592.41
Volume:	639.314
LogP:	7.164
LogD:	4.85
LogS:	-5.624
# Rotatable Bonds:	2
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.242
Synthetic Accessibility Score:	5.25
Fsp3:	0.816
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.08
MDCK Permeability:	1.6120142390718684e-05
Pgp-inhibitor:	0.965
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.881
30% Bioavailability (F30%):	0.89

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.178
Plasma Protein Binding (PPB):	95.74213409423828%
Volume Distribution (VD):	1.024
Pgp-substrate:	3.1312811374664307%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.4
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.873
CYP2C9-inhibitor:	0.098
CYP2C9-substrate:	0.146
CYP2D6-inhibitor:	0.123
CYP2D6-substrate:	0.552
CYP3A4-inhibitor:	0.211
CYP3A4-substrate:	0.371

ADMET: Excretion

Clearance (CL):	5.874
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.5
Human Hepatotoxicity (H-HT):	0.232
Drug-inuced Liver Injury (DILI):	0.025
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.161
Maximum Recommended Daily Dose:	0.949
Skin Sensitization:	0.921
Carcinogencity:	0.161
Eye Corrosion:	0.003
Eye Irritation:	0.193
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC477206

Natural Product ID:	NPC477206
*Common Name:**	Halicloic Acid A
IUPAC Name:	2-hydroxy-2-[(1R,2S,5S,13S,14R,17R,18S,21S,26S,28S)-10-hydroxy-1,5,14,18,22,22,26-heptamethyl-27-oxaheptacyclo[15.13.0.02,14.05,13.06,11.018,28.021,26]triaconta-6,8,10-trien-7-yl]acetic acid
Synonyms:	Halicloic Acid A
Standard InCHIKey:	NAKUKBFDSKFFRM-PDDLSVGESA-N
Standard InCHI:	InChI=1S/C38H56O5/c1-33(2)15-8-16-38(7)25(33)11-18-36(5)27-12-17-35(4)26(34(27,3)20-14-29(36)43-38)13-19-37(6)28(35)21-23-24(39)10-9-22(30(23)37)31(40)32(41)42/h9-10,25-29,31,39-40H,8,11-21H2,1-7H3,(H,41,42)/t25-,26+,27+,28-,29-,31?,34+,35+,36-,37-,38-/m0/s1
SMILES:	C[C@]12CC[C@H]3[C@]([C@@H]1CC[C@@]4([C@@H]2CC[C@]5([C@H]4CC6=C(C=CC(=C65)C(C(=O)O)O)O)C)C)(CC[C@@H]7[C@@](O3)(CCCC7(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	66553577
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000020] Fluorenes

*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
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575970]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17848089]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	Pacific	n.a.	PMID[19133758]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	Culasian Point, Leyte, Philippines (S 1119.00', E 12435.60')	1991-MAR	PMID[22873824]
NPO33502	Haliclona sp.	Species	Chalinidae	Eukaryota	n.a.	New Zealand	n.a.	PMID[24128145]

☑ 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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1078	Individual Protein	Indoleamine 2,3-dioxygenase	Homo sapiens	IC50	=	10000	nM	PMID[22873824]

☑ 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 NPC477206 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	338
0.1-0.2	1332
0.2-0.3	2819
0.3-0.4	5894
0.4-0.5	9885
0.5-0.6	13162
0.6-0.7	8366
0.7-0.8	825
0.8-0.85	72
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9507	High Similarity	NPC477207
0.8667	High Similarity	NPC477208
0.863	High Similarity	NPC248287
0.863	High Similarity	NPC234548
0.86	High Similarity	NPC8102
0.86	High Similarity	NPC66894
0.8553	High Similarity	NPC279442
0.8456	Intermediate Similarity	NPC2681
0.8456	Intermediate Similarity	NPC272907
0.8425	Intermediate Similarity	NPC472804
0.8425	Intermediate Similarity	NPC279463
0.8425	Intermediate Similarity	NPC103082
0.8389	Intermediate Similarity	NPC172311
0.8389	Intermediate Similarity	NPC304110
0.8389	Intermediate Similarity	NPC27518
0.8367	Intermediate Similarity	NPC249817
0.8356	Intermediate Similarity	NPC11266
0.8344	Intermediate Similarity	NPC25491
0.8333	Intermediate Similarity	NPC35212
0.8311	Intermediate Similarity	NPC477592
0.8311	Intermediate Similarity	NPC22676
0.8311	Intermediate Similarity	NPC216940
0.8311	Intermediate Similarity	NPC475482
0.8311	Intermediate Similarity	NPC198621
0.8299	Intermediate Similarity	NPC477874
0.8299	Intermediate Similarity	NPC173569
0.8288	Intermediate Similarity	NPC475627
0.8288	Intermediate Similarity	NPC475346
0.8288	Intermediate Similarity	NPC475457
0.8288	Intermediate Similarity	NPC18982
0.8288	Intermediate Similarity	NPC476282
0.8288	Intermediate Similarity	NPC49742
0.8278	Intermediate Similarity	NPC477209
0.8278	Intermediate Similarity	NPC310621
0.8278	Intermediate Similarity	NPC252133
0.8278	Intermediate Similarity	NPC477873
0.8278	Intermediate Similarity	NPC469447
0.8267	Intermediate Similarity	NPC473612
0.8267	Intermediate Similarity	NPC3218
0.8228	Intermediate Similarity	NPC472807
0.8217	Intermediate Similarity	NPC105942
0.8217	Intermediate Similarity	NPC205392
0.8182	Intermediate Similarity	NPC472938
0.8182	Intermediate Similarity	NPC472936
0.8182	Intermediate Similarity	NPC472937
0.817	Intermediate Similarity	NPC126707
0.817	Intermediate Similarity	NPC53520
0.8151	Intermediate Similarity	NPC243305
0.8146	Intermediate Similarity	NPC472801
0.8133	Intermediate Similarity	NPC139243
0.8133	Intermediate Similarity	NPC116742
0.8133	Intermediate Similarity	NPC477593
0.8129	Intermediate Similarity	NPC477483
0.8129	Intermediate Similarity	NPC325032
0.8125	Intermediate Similarity	NPC262936
0.8125	Intermediate Similarity	NPC30491
0.8112	Intermediate Similarity	NPC87985
0.811	Intermediate Similarity	NPC200726
0.8108	Intermediate Similarity	NPC477594
0.8105	Intermediate Similarity	NPC96447
0.8092	Intermediate Similarity	NPC477595
0.8089	Intermediate Similarity	NPC77310
0.8079	Intermediate Similarity	NPC470616
0.8079	Intermediate Similarity	NPC470617
0.8065	Intermediate Similarity	NPC474991
0.8061	Intermediate Similarity	NPC177362
0.8054	Intermediate Similarity	NPC477596
0.8039	Intermediate Similarity	NPC235557
0.8028	Intermediate Similarity	NPC121168
0.8025	Intermediate Similarity	NPC327962
0.8025	Intermediate Similarity	NPC472939
0.8013	Intermediate Similarity	NPC5568
0.8013	Intermediate Similarity	NPC182249
0.8012	Intermediate Similarity	NPC266545
0.8012	Intermediate Similarity	NPC202428
0.7988	Intermediate Similarity	NPC161151
0.7987	Intermediate Similarity	NPC26045
0.7975	Intermediate Similarity	NPC118033
0.7975	Intermediate Similarity	NPC261659
0.7962	Intermediate Similarity	NPC473719
0.7962	Intermediate Similarity	NPC253591
0.7961	Intermediate Similarity	NPC164743
0.7961	Intermediate Similarity	NPC271494
0.7961	Intermediate Similarity	NPC473591
0.7961	Intermediate Similarity	NPC155192
0.7958	Intermediate Similarity	NPC249340
0.7958	Intermediate Similarity	NPC162935
0.795	Intermediate Similarity	NPC10945
0.7949	Intermediate Similarity	NPC246229
0.7949	Intermediate Similarity	NPC191899
0.7933	Intermediate Similarity	NPC43353
0.7925	Intermediate Similarity	NPC475579
0.7925	Intermediate Similarity	NPC473773
0.7922	Intermediate Similarity	NPC184935
0.7917	Intermediate Similarity	NPC181334
0.7911	Intermediate Similarity	NPC142654
0.7905	Intermediate Similarity	NPC476847
0.7902	Intermediate Similarity	NPC478058
0.7898	Intermediate Similarity	NPC127046
0.7891	Intermediate Similarity	NPC86257
0.7887	Intermediate Similarity	NPC241001
0.7885	Intermediate Similarity	NPC84786
0.7885	Intermediate Similarity	NPC470038
0.7879	Intermediate Similarity	NPC471861
0.7872	Intermediate Similarity	NPC42657
0.7871	Intermediate Similarity	NPC478164
0.7867	Intermediate Similarity	NPC293454
0.7862	Intermediate Similarity	NPC473680
0.7862	Intermediate Similarity	NPC475311
0.7862	Intermediate Similarity	NPC475454
0.7862	Intermediate Similarity	NPC473579
0.7857	Intermediate Similarity	NPC91019
0.7857	Intermediate Similarity	NPC106519
0.7848	Intermediate Similarity	NPC106524
0.7848	Intermediate Similarity	NPC290695
0.7847	Intermediate Similarity	NPC471187
0.7847	Intermediate Similarity	NPC198014
0.7832	Intermediate Similarity	NPC253627
0.7829	Intermediate Similarity	NPC471152
0.7821	Intermediate Similarity	NPC473602
0.7817	Intermediate Similarity	NPC478121
0.7817	Intermediate Similarity	NPC190501
0.7817	Intermediate Similarity	NPC318552
0.7812	Intermediate Similarity	NPC48671
0.7808	Intermediate Similarity	NPC269598
0.7806	Intermediate Similarity	NPC248068
0.78	Intermediate Similarity	NPC78307
0.7799	Intermediate Similarity	NPC247219
0.7792	Intermediate Similarity	NPC470035
0.7785	Intermediate Similarity	NPC18798
0.7785	Intermediate Similarity	NPC52161
0.7785	Intermediate Similarity	NPC162751
0.7778	Intermediate Similarity	NPC11250
0.7771	Intermediate Similarity	NPC478160
0.777	Intermediate Similarity	NPC475138
0.777	Intermediate Similarity	NPC131684
0.7764	Intermediate Similarity	NPC474533
0.7764	Intermediate Similarity	NPC474534
0.7763	Intermediate Similarity	NPC262324
0.7762	Intermediate Similarity	NPC328504
0.7762	Intermediate Similarity	NPC164852
0.7758	Intermediate Similarity	NPC266365
0.7756	Intermediate Similarity	NPC474599
0.7751	Intermediate Similarity	NPC472803
0.775	Intermediate Similarity	NPC140133
0.775	Intermediate Similarity	NPC470037
0.7748	Intermediate Similarity	NPC471864
0.7746	Intermediate Similarity	NPC79933
0.7746	Intermediate Similarity	NPC126002
0.7746	Intermediate Similarity	NPC258366
0.7746	Intermediate Similarity	NPC31296
0.7746	Intermediate Similarity	NPC473974
0.7744	Intermediate Similarity	NPC471750
0.774	Intermediate Similarity	NPC137416
0.774	Intermediate Similarity	NPC137750
0.7736	Intermediate Similarity	NPC94781
0.7736	Intermediate Similarity	NPC298647
0.7736	Intermediate Similarity	NPC273358
0.7736	Intermediate Similarity	NPC292206
0.7733	Intermediate Similarity	NPC165612
0.7727	Intermediate Similarity	NPC79372
0.7722	Intermediate Similarity	NPC472134
0.7722	Intermediate Similarity	NPC63918
0.7722	Intermediate Similarity	NPC120536
0.7718	Intermediate Similarity	NPC472793
0.7716	Intermediate Similarity	NPC474622
0.7716	Intermediate Similarity	NPC474621
0.7712	Intermediate Similarity	NPC49911
0.7712	Intermediate Similarity	NPC475957
0.7711	Intermediate Similarity	NPC471850
0.7708	Intermediate Similarity	NPC293831
0.7708	Intermediate Similarity	NPC77569
0.7708	Intermediate Similarity	NPC369
0.7708	Intermediate Similarity	NPC142198
0.7708	Intermediate Similarity	NPC475166
0.7707	Intermediate Similarity	NPC235195
0.7707	Intermediate Similarity	NPC19862
0.7703	Intermediate Similarity	NPC229894
0.7702	Intermediate Similarity	NPC477276
0.7692	Intermediate Similarity	NPC308572
0.7692	Intermediate Similarity	NPC85310
0.7692	Intermediate Similarity	NPC68339
0.7688	Intermediate Similarity	NPC470619
0.7688	Intermediate Similarity	NPC208785
0.7688	Intermediate Similarity	NPC470618
0.7688	Intermediate Similarity	NPC145527
0.7682	Intermediate Similarity	NPC48929
0.7676	Intermediate Similarity	NPC471671
0.7676	Intermediate Similarity	NPC469609
0.7674	Intermediate Similarity	NPC475613
0.7673	Intermediate Similarity	NPC215593
0.7673	Intermediate Similarity	NPC96930
0.7673	Intermediate Similarity	NPC32017
0.7671	Intermediate Similarity	NPC10154
0.7671	Intermediate Similarity	NPC15127
0.7671	Intermediate Similarity	NPC265413
0.7669	Intermediate Similarity	NPC474501
0.7662	Intermediate Similarity	NPC265335
0.7662	Intermediate Similarity	NPC79921
0.766	Intermediate Similarity	NPC137496

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 NPC477206 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	289
0.1-0.2	844
0.2-0.3	1621
0.3-0.4	2847
0.4-0.5	2117
0.5-0.6	1113
0.6-0.7	309
0.7-0.8	9
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8276	Intermediate Similarity	NPD6663	Approved
0.8252	Intermediate Similarity	NPD5736	Approved
0.8092	Intermediate Similarity	NPD8166	Discontinued
0.7817	Intermediate Similarity	NPD3019	Approved
0.7708	Intermediate Similarity	NPD3092	Approved
0.7692	Intermediate Similarity	NPD2932	Approved
0.7662	Intermediate Similarity	NPD5762	Approved
0.7662	Intermediate Similarity	NPD5763	Approved
0.7651	Intermediate Similarity	NPD8127	Discontinued
0.7619	Intermediate Similarity	NPD3094	Phase 2
0.761	Intermediate Similarity	NPD6273	Approved
0.7552	Intermediate Similarity	NPD3091	Approved
0.7516	Intermediate Similarity	NPD7003	Approved
0.7451	Intermediate Similarity	NPD6355	Discontinued
0.7438	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD8032	Phase 2
0.7397	Intermediate Similarity	NPD3023	Approved
0.7397	Intermediate Similarity	NPD3026	Approved
0.7394	Intermediate Similarity	NPD2629	Approved
0.7386	Intermediate Similarity	NPD4060	Phase 1
0.7386	Intermediate Similarity	NPD4140	Approved
0.7379	Intermediate Similarity	NPD3025	Approved
0.7379	Intermediate Similarity	NPD3024	Approved
0.7372	Intermediate Similarity	NPD5408	Approved
0.7372	Intermediate Similarity	NPD5406	Approved
0.7372	Intermediate Similarity	NPD5405	Approved
0.7372	Intermediate Similarity	NPD5404	Approved
0.7362	Intermediate Similarity	NPD7458	Discontinued
0.7358	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3095	Discontinued
0.7312	Intermediate Similarity	NPD7236	Approved
0.7288	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD8150	Discontinued
0.7226	Intermediate Similarity	NPD5735	Approved
0.7222	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD4059	Approved
0.719	Intermediate Similarity	NPD7095	Approved
0.7186	Intermediate Similarity	NPD8455	Phase 2
0.7182	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8312	Approved
0.7175	Intermediate Similarity	NPD8313	Approved
0.7143	Intermediate Similarity	NPD3764	Approved
0.7143	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6798	Discontinued
0.7126	Intermediate Similarity	NPD7228	Approved
0.7097	Intermediate Similarity	NPD7961	Discontinued
0.7091	Intermediate Similarity	NPD7239	Suspended
0.7086	Intermediate Similarity	NPD1283	Approved
0.7081	Intermediate Similarity	NPD4628	Phase 3
0.7075	Intermediate Similarity	NPD7741	Discontinued
0.7072	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7390	Discontinued
0.7052	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD3620	Phase 2
0.7051	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6190	Approved
0.7035	Intermediate Similarity	NPD7199	Phase 2
0.7024	Intermediate Similarity	NPD37	Approved
0.7018	Intermediate Similarity	NPD6234	Discontinued
0.7	Intermediate Similarity	NPD4966	Approved
0.7	Intermediate Similarity	NPD4965	Approved
0.7	Intermediate Similarity	NPD4967	Phase 2
0.7	Intermediate Similarity	NPD1201	Approved
0.6981	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD4110	Phase 3
0.6975	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6353	Approved
0.6943	Remote Similarity	NPD2979	Phase 3
0.6937	Remote Similarity	NPD2438	Suspended
0.6937	Remote Similarity	NPD4477	Approved
0.6937	Remote Similarity	NPD4476	Approved
0.6928	Remote Similarity	NPD1470	Approved
0.6918	Remote Similarity	NPD7097	Phase 1
0.6909	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD5327	Phase 3
0.6901	Remote Similarity	NPD7768	Phase 2
0.6894	Remote Similarity	NPD6004	Phase 3
0.6894	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD6002	Phase 3
0.6894	Remote Similarity	NPD6005	Phase 3
0.6893	Remote Similarity	NPD5844	Phase 1
0.689	Remote Similarity	NPD3300	Phase 2
0.6887	Remote Similarity	NPD1281	Approved
0.6883	Remote Similarity	NPD4624	Approved
0.6882	Remote Similarity	NPD7819	Suspended
0.6875	Remote Similarity	NPD7743	Approved
0.6875	Remote Similarity	NPD7742	Approved
0.6871	Remote Similarity	NPD4198	Discontinued
0.686	Remote Similarity	NPD7075	Discontinued
0.6859	Remote Similarity	NPD8319	Approved
0.6859	Remote Similarity	NPD8320	Phase 1
0.6859	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7799	Discontinued
0.6832	Remote Similarity	NPD6099	Approved
0.6832	Remote Similarity	NPD6100	Approved
0.6826	Remote Similarity	NPD7427	Discontinued
0.6816	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7028	Phase 2
0.6784	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7473	Discontinued
0.6778	Remote Similarity	NPD7240	Approved
0.6778	Remote Similarity	NPD7685	Pre-registration
0.6776	Remote Similarity	NPD8434	Phase 2
0.6774	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6233	Phase 2
0.677	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.677	Remote Similarity	NPD7033	Discontinued
0.677	Remote Similarity	NPD2799	Discontinued
0.6765	Remote Similarity	NPD6677	Suspended
0.6755	Remote Similarity	NPD4626	Approved
0.6752	Remote Similarity	NPD7008	Discontinued
0.675	Remote Similarity	NPD6653	Approved
0.6744	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6959	Discontinued
0.6735	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD2861	Phase 2
0.6728	Remote Similarity	NPD2531	Phase 2
0.6728	Remote Similarity	NPD2935	Discontinued
0.6727	Remote Similarity	NPD8131	Suspended
0.672	Remote Similarity	NPD7700	Phase 2
0.672	Remote Similarity	NPD7699	Phase 2
0.6719	Remote Similarity	NPD7435	Discontinued
0.6707	Remote Similarity	NPD2534	Approved
0.6707	Remote Similarity	NPD2532	Approved
0.6707	Remote Similarity	NPD2533	Approved
0.6705	Remote Similarity	NPD3787	Discontinued
0.6705	Remote Similarity	NPD7058	Phase 2
0.6705	Remote Similarity	NPD6232	Discontinued
0.6705	Remote Similarity	NPD7057	Phase 3
0.6705	Remote Similarity	NPD7229	Phase 3
0.6704	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD5691	Approved
0.6689	Remote Similarity	NPD5951	Approved
0.6687	Remote Similarity	NPD7266	Discontinued
0.6686	Remote Similarity	NPD4666	Phase 3
0.6667	Remote Similarity	NPD7094	Approved
0.6667	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3400	Discontinued
0.6667	Remote Similarity	NPD7714	Approved
0.6667	Remote Similarity	NPD7635	Approved
0.6667	Remote Similarity	NPD3750	Approved
0.6667	Remote Similarity	NPD6858	Approved
0.6667	Remote Similarity	NPD7715	Approved
0.6649	Remote Similarity	NPD6534	Approved
0.6649	Remote Similarity	NPD6535	Approved
0.6647	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD3226	Approved
0.6646	Remote Similarity	NPD5958	Discontinued
0.6646	Remote Similarity	NPD4534	Discontinued
0.6646	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD8651	Approved
0.6632	Remote Similarity	NPD7497	Discontinued
0.6629	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD5709	Phase 3
0.6629	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6166	Phase 2
0.6629	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6801	Discontinued
0.6623	Remote Similarity	NPD1608	Approved
0.6609	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6608	Remote Similarity	NPD6599	Discontinued
0.6608	Remote Similarity	NPD4380	Phase 2
0.6606	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6674	Discontinued
0.6604	Remote Similarity	NPD7985	Registered
0.6604	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD7874	Approved
0.6599	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD7870	Phase 2
0.6598	Remote Similarity	NPD7871	Phase 2
0.6593	Remote Similarity	NPD6765	Approved
0.6593	Remote Similarity	NPD6764	Approved
0.659	Remote Similarity	NPD5761	Phase 2
0.659	Remote Similarity	NPD5760	Phase 2
0.659	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD2346	Discontinued
0.6581	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD1651	Approved
0.6578	Remote Similarity	NPD2490	Approved
0.6578	Remote Similarity	NPD2488	Approved
0.6575	Remote Similarity	NPD3021	Approved
0.6575	Remote Similarity	NPD3022	Approved
0.6564	Remote Similarity	NPD7305	Phase 1
0.6562	Remote Similarity	NPD6781	Approved
0.6562	Remote Similarity	NPD6777	Approved
0.6562	Remote Similarity	NPD6780	Approved
0.6562	Remote Similarity	NPD4062	Phase 3
0.6562	Remote Similarity	NPD6776	Approved
0.6562	Remote Similarity	NPD6778	Approved
0.6562	Remote Similarity	NPD6779	Approved
0.6562	Remote Similarity	NPD4248	Discontinued
0.6562	Remote Similarity	NPD6782	Approved
0.6561	Remote Similarity	NPD5647	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