NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	592.41
Volume:	645.234
LogP:	6.299
LogD:	4.542
LogS:	-4.959
# Rotatable Bonds:	5
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.162
Synthetic Accessibility Score:	5.424
Fsp3:	0.763
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:	-5.086
MDCK Permeability:	1.941999107657466e-05
Pgp-inhibitor:	0.918
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.971
30% Bioavailability (F30%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.173
Plasma Protein Binding (PPB):	96.76252746582031%
Volume Distribution (VD):	0.995
Pgp-substrate:	2.7771904468536377%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.278
CYP2C19-inhibitor:	0.029
CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.127
CYP2C9-substrate:	0.109
CYP2D6-inhibitor:	0.136
CYP2D6-substrate:	0.143
CYP3A4-inhibitor:	0.363
CYP3A4-substrate:	0.341

ADMET: Excretion

Clearance (CL):	6.353
Half-life (T1/2):	0.203

ADMET: Toxicity

hERG Blockers:	0.482
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.024
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.122
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.926
Carcinogencity:	0.086
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.943

Download Data

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

Natural Product: NPC477207

Natural Product ID:	NPC477207
*Common Name:**	Halicloic acid B
IUPAC Name:	2-[(1S,2S,4aR,4bS,6aS,11aS,11bR,13aR)-2,10-dihydroxy-1,4a,6a,11b-tetramethyl-1-[2-[(1S,6R)-1,2,6-trimethylcyclohex-2-en-1-yl]ethyl]-3,4,4b,5,6,11,11a,12,13,13a-decahydro-2H-indeno[2,1-a]phenanthren-7-yl]-2-hydroxyacetic acid
Synonyms:	Rel-Halicloic Acid B
Standard InCHIKey:	BIWPAJKWWZONNW-MQNCUHRTSA-N
Standard InCHI:	InChI=1S/C38H56O5/c1-22-9-8-10-23(2)34(22,3)19-20-37(6)28-13-16-36(5)27(35(28,4)18-15-30(37)40)14-17-38(7)29(36)21-25-26(39)12-11-24(31(25)38)32(41)33(42)43/h9,11-12,23,27-30,32,39-41H,8,10,13-21H2,1-7H3,(H,42,43)/t23-,27-,28-,29+,30+,32?,34-,35-,36-,37+,38+/m1/s1
SMILES:	C[C@@H]1CCC=C([C@@]1(C)CC[C@]2([C@@H]3CC[C@@]4([C@@H]([C@]3(CC[C@@H]2O)C)CC[C@]5([C@H]4CC6=C(C=CC(=C65)C(C(=O)O)O)O)C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	66553578
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid 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
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	=	11000	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 NPC477207 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	312
0.1-0.2	1236
0.2-0.3	2606
0.3-0.4	5635
0.4-0.5	9141
0.5-0.6	12311
0.6-0.7	10112
0.7-0.8	1239
0.8-0.85	93
0.85-0.9	10
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9507	High Similarity	NPC477206
0.869	High Similarity	NPC477209
0.8601	High Similarity	NPC477592
0.8592	High Similarity	NPC103082
0.8582	High Similarity	NPC475346
0.8582	High Similarity	NPC476282
0.8582	High Similarity	NPC475627
0.8582	High Similarity	NPC18982
0.8582	High Similarity	NPC475457
0.8571	High Similarity	NPC243305
0.8542	High Similarity	NPC234548
0.8542	High Similarity	NPC248287
0.8514	High Similarity	NPC66894
0.8514	High Similarity	NPC8102
0.8493	Intermediate Similarity	NPC272907
0.8493	Intermediate Similarity	NPC2681
0.8467	Intermediate Similarity	NPC279442
0.8462	Intermediate Similarity	NPC472804
0.8425	Intermediate Similarity	NPC304110
0.8425	Intermediate Similarity	NPC27518
0.8417	Intermediate Similarity	NPC30491
0.8417	Intermediate Similarity	NPC262936
0.8414	Intermediate Similarity	NPC477593
0.8406	Intermediate Similarity	NPC87985
0.8403	Intermediate Similarity	NPC249817
0.8392	Intermediate Similarity	NPC477594
0.8345	Intermediate Similarity	NPC475482
0.8345	Intermediate Similarity	NPC22676
0.8345	Intermediate Similarity	NPC216940
0.8345	Intermediate Similarity	NPC198621
0.8333	Intermediate Similarity	NPC279463
0.8333	Intermediate Similarity	NPC477596
0.8333	Intermediate Similarity	NPC477874
0.8333	Intermediate Similarity	NPC173569
0.8322	Intermediate Similarity	NPC49742
0.8311	Intermediate Similarity	NPC477873
0.8311	Intermediate Similarity	NPC469447
0.8299	Intermediate Similarity	NPC172311
0.8299	Intermediate Similarity	NPC3218
0.8288	Intermediate Similarity	NPC139243
0.8288	Intermediate Similarity	NPC116742
0.8264	Intermediate Similarity	NPC11266
0.8255	Intermediate Similarity	NPC25491
0.8248	Intermediate Similarity	NPC249340
0.8248	Intermediate Similarity	NPC162935
0.8243	Intermediate Similarity	NPC35212
0.8243	Intermediate Similarity	NPC477595
0.8231	Intermediate Similarity	NPC470616
0.8231	Intermediate Similarity	NPC470617
0.8212	Intermediate Similarity	NPC472936
0.8212	Intermediate Similarity	NPC477208
0.8212	Intermediate Similarity	NPC472937
0.8212	Intermediate Similarity	NPC472938
0.8207	Intermediate Similarity	NPC43353
0.8201	Intermediate Similarity	NPC181334
0.82	Intermediate Similarity	NPC126707
0.82	Intermediate Similarity	NPC53520
0.8188	Intermediate Similarity	NPC310621
0.8188	Intermediate Similarity	NPC252133
0.8188	Intermediate Similarity	NPC121168
0.8188	Intermediate Similarity	NPC235557
0.8188	Intermediate Similarity	NPC184935
0.8182	Intermediate Similarity	NPC18798
0.8176	Intermediate Similarity	NPC473612
0.8176	Intermediate Similarity	NPC472801
0.8175	Intermediate Similarity	NPC241001
0.8162	Intermediate Similarity	NPC42657
0.8158	Intermediate Similarity	NPC477483
0.8158	Intermediate Similarity	NPC325032
0.8138	Intermediate Similarity	NPC293454
0.8133	Intermediate Similarity	NPC26045
0.8129	Intermediate Similarity	NPC105942
0.8129	Intermediate Similarity	NPC198014
0.8129	Intermediate Similarity	NPC471187
0.8129	Intermediate Similarity	NPC205392
0.8121	Intermediate Similarity	NPC91019
0.8121	Intermediate Similarity	NPC106519
0.8117	Intermediate Similarity	NPC77310
0.8117	Intermediate Similarity	NPC261659
0.8116	Intermediate Similarity	NPC253627
0.8105	Intermediate Similarity	NPC253591
0.8102	Intermediate Similarity	NPC190501
0.8102	Intermediate Similarity	NPC318552
0.8092	Intermediate Similarity	NPC474991
0.8085	Intermediate Similarity	NPC269598
0.8069	Intermediate Similarity	NPC78307
0.8067	Intermediate Similarity	NPC248068
0.8058	Intermediate Similarity	NPC478058
0.8058	Intermediate Similarity	NPC11250
0.8056	Intermediate Similarity	NPC476847
0.8052	Intermediate Similarity	NPC327962
0.8052	Intermediate Similarity	NPC142654
0.8052	Intermediate Similarity	NPC472939
0.8043	Intermediate Similarity	NPC259703
0.8043	Intermediate Similarity	NPC32322
0.8043	Intermediate Similarity	NPC328504
0.8042	Intermediate Similarity	NPC117899
0.8041	Intermediate Similarity	NPC182249
0.8039	Intermediate Similarity	NPC5568
0.8029	Intermediate Similarity	NPC31296
0.8029	Intermediate Similarity	NPC258366
0.8029	Intermediate Similarity	NPC79933
0.8029	Intermediate Similarity	NPC473974
0.8025	Intermediate Similarity	NPC200726
0.8014	Intermediate Similarity	NPC471913
0.8014	Intermediate Similarity	NPC137750
0.8013	Intermediate Similarity	NPC478164
0.8013	Intermediate Similarity	NPC96447
0.8012	Intermediate Similarity	NPC161151
0.8	Intermediate Similarity	NPC118033
0.8	Intermediate Similarity	NPC475454
0.8	Intermediate Similarity	NPC475311
0.8	Intermediate Similarity	NPC473680
0.8	Intermediate Similarity	NPC473579
0.7987	Intermediate Similarity	NPC473719
0.7987	Intermediate Similarity	NPC473591
0.7987	Intermediate Similarity	NPC271494
0.7987	Intermediate Similarity	NPC155192
0.7986	Intermediate Similarity	NPC77569
0.7986	Intermediate Similarity	NPC142198
0.7975	Intermediate Similarity	NPC10945
0.7975	Intermediate Similarity	NPC177362
0.7974	Intermediate Similarity	NPC191899
0.7974	Intermediate Similarity	NPC246229
0.7973	Intermediate Similarity	NPC277559
0.7973	Intermediate Similarity	NPC471152
0.7973	Intermediate Similarity	NPC475957
0.7972	Intermediate Similarity	NPC229894
0.7972	Intermediate Similarity	NPC193203
0.7971	Intermediate Similarity	NPC68339
0.7971	Intermediate Similarity	NPC478121
0.7958	Intermediate Similarity	NPC471930
0.7958	Intermediate Similarity	NPC71610
0.7958	Intermediate Similarity	NPC471929
0.7958	Intermediate Similarity	NPC471935
0.7956	Intermediate Similarity	NPC469609
0.7956	Intermediate Similarity	NPC471671
0.7949	Intermediate Similarity	NPC475579
0.7949	Intermediate Similarity	NPC473773
0.7943	Intermediate Similarity	NPC15127
0.7941	Intermediate Similarity	NPC154511
0.7941	Intermediate Similarity	NPC137496
0.7941	Intermediate Similarity	NPC257540
0.7941	Intermediate Similarity	NPC474358
0.7941	Intermediate Similarity	NPC474387
0.7941	Intermediate Similarity	NPC247858
0.7929	Intermediate Similarity	NPC471794
0.7929	Intermediate Similarity	NPC176208
0.7927	Intermediate Similarity	NPC202428
0.7927	Intermediate Similarity	NPC266545
0.7922	Intermediate Similarity	NPC52161
0.7922	Intermediate Similarity	NPC162751
0.7922	Intermediate Similarity	NPC127046
0.7917	Intermediate Similarity	NPC131684
0.7917	Intermediate Similarity	NPC86257
0.7914	Intermediate Similarity	NPC164852
0.7911	Intermediate Similarity	NPC472807
0.7908	Intermediate Similarity	NPC478160
0.7908	Intermediate Similarity	NPC84786
0.7908	Intermediate Similarity	NPC470038
0.7905	Intermediate Similarity	NPC262324
0.7901	Intermediate Similarity	NPC471861
0.7899	Intermediate Similarity	NPC93071
0.7899	Intermediate Similarity	NPC469644
0.7895	Intermediate Similarity	NPC199936
0.7891	Intermediate Similarity	NPC471864
0.7883	Intermediate Similarity	NPC477136
0.7883	Intermediate Similarity	NPC304510
0.7883	Intermediate Similarity	NPC172219
0.7877	Intermediate Similarity	NPC165612
0.7875	Intermediate Similarity	NPC471750
0.7871	Intermediate Similarity	NPC290695
0.7871	Intermediate Similarity	NPC106524
0.7868	Intermediate Similarity	NPC147179
0.7867	Intermediate Similarity	NPC164743
0.7857	Intermediate Similarity	NPC293831
0.7857	Intermediate Similarity	NPC369
0.7857	Intermediate Similarity	NPC475166
0.7857	Intermediate Similarity	NPC154696
0.7852	Intermediate Similarity	NPC49911
0.7842	Intermediate Similarity	NPC183339
0.7842	Intermediate Similarity	NPC234337
0.7842	Intermediate Similarity	NPC133389
0.7826	Intermediate Similarity	NPC154030
0.7826	Intermediate Similarity	NPC164649
0.7826	Intermediate Similarity	NPC48342
0.7821	Intermediate Similarity	NPC145527
0.7821	Intermediate Similarity	NPC470619
0.7821	Intermediate Similarity	NPC247219
0.7821	Intermediate Similarity	NPC208785
0.7821	Intermediate Similarity	NPC470618
0.7815	Intermediate Similarity	NPC471853
0.7815	Intermediate Similarity	NPC470035
0.781	Intermediate Similarity	NPC38893
0.781	Intermediate Similarity	NPC477137
0.781	Intermediate Similarity	NPC308828
0.781	Intermediate Similarity	NPC308311
0.781	Intermediate Similarity	NPC219112
0.7808	Intermediate Similarity	NPC291001
0.7808	Intermediate Similarity	NPC471851

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 NPC477207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	262
0.1-0.2	814
0.2-0.3	1509
0.3-0.4	2758
0.4-0.5	2100
0.5-0.6	1272
0.6-0.7	399
0.7-0.8	35
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
0.831	Intermediate Similarity	NPD6663	Approved
0.8286	Intermediate Similarity	NPD5736	Approved
0.8121	Intermediate Similarity	NPD8166	Discontinued
0.8102	Intermediate Similarity	NPD3019	Approved
0.8102	Intermediate Similarity	NPD2932	Approved
0.7986	Intermediate Similarity	NPD3092	Approved
0.7887	Intermediate Similarity	NPD3094	Phase 2
0.7826	Intermediate Similarity	NPD3091	Approved
0.7682	Intermediate Similarity	NPD5762	Approved
0.7682	Intermediate Similarity	NPD5763	Approved
0.7669	Intermediate Similarity	NPD8127	Discontinued
0.766	Intermediate Similarity	NPD3026	Approved
0.766	Intermediate Similarity	NPD3023	Approved
0.7643	Intermediate Similarity	NPD3025	Approved
0.7643	Intermediate Similarity	NPD3024	Approved
0.7628	Intermediate Similarity	NPD6273	Approved
0.7616	Intermediate Similarity	NPD5406	Approved
0.7616	Intermediate Similarity	NPD5408	Approved
0.7616	Intermediate Similarity	NPD5405	Approved
0.7616	Intermediate Similarity	NPD5404	Approved
0.7597	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD3095	Discontinued
0.7532	Intermediate Similarity	NPD7003	Approved
0.7467	Intermediate Similarity	NPD6355	Discontinued
0.7452	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD8032	Phase 2
0.741	Intermediate Similarity	NPD2629	Approved
0.74	Intermediate Similarity	NPD4140	Approved
0.74	Intermediate Similarity	NPD4060	Phase 1
0.7375	Intermediate Similarity	NPD7458	Discontinued
0.7343	Intermediate Similarity	NPD4059	Approved
0.7325	Intermediate Similarity	NPD7236	Approved
0.7257	Intermediate Similarity	NPD8150	Discontinued
0.7256	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1201	Approved
0.7237	Intermediate Similarity	NPD5735	Approved
0.7211	Intermediate Similarity	NPD1283	Approved
0.7208	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD8455	Phase 2
0.7171	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3620	Phase 2
0.717	Intermediate Similarity	NPD7390	Discontinued
0.7162	Intermediate Similarity	NPD1470	Approved
0.7152	Intermediate Similarity	NPD6798	Discontinued
0.7135	Intermediate Similarity	NPD7228	Approved
0.7134	Intermediate Similarity	NPD37	Approved
0.7107	Intermediate Similarity	NPD3300	Phase 2
0.7102	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7239	Suspended
0.7097	Intermediate Similarity	NPD7742	Approved
0.7097	Intermediate Similarity	NPD7743	Approved
0.7095	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD4628	Phase 3
0.7086	Intermediate Similarity	NPD8312	Approved
0.7086	Intermediate Similarity	NPD7095	Approved
0.7086	Intermediate Similarity	NPD8313	Approved
0.7079	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7199	Phase 2
0.7039	Intermediate Similarity	NPD3764	Approved
0.7024	Intermediate Similarity	NPD6234	Discontinued
0.7007	Intermediate Similarity	NPD1281	Approved
0.7006	Intermediate Similarity	NPD4967	Phase 2
0.7006	Intermediate Similarity	NPD4965	Approved
0.7006	Intermediate Similarity	NPD4966	Approved
0.6993	Remote Similarity	NPD7961	Discontinued
0.6987	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD4110	Phase 3
0.6981	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7741	Discontinued
0.6948	Remote Similarity	NPD2979	Phase 3
0.6943	Remote Similarity	NPD2438	Suspended
0.6937	Remote Similarity	NPD6190	Approved
0.6923	Remote Similarity	NPD5951	Approved
0.6914	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD5327	Phase 3
0.6909	Remote Similarity	NPD7028	Phase 2
0.6905	Remote Similarity	NPD7768	Phase 2
0.6901	Remote Similarity	NPD7635	Approved
0.6899	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6005	Phase 3
0.6899	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6004	Phase 3
0.6899	Remote Similarity	NPD6002	Phase 3
0.6897	Remote Similarity	NPD5844	Phase 1
0.6887	Remote Similarity	NPD4624	Approved
0.6886	Remote Similarity	NPD7819	Suspended
0.6879	Remote Similarity	NPD7473	Discontinued
0.6875	Remote Similarity	NPD3400	Discontinued
0.6871	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD4626	Approved
0.6864	Remote Similarity	NPD7075	Discontinued
0.6863	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD7008	Discontinued
0.6859	Remote Similarity	NPD6353	Approved
0.6839	Remote Similarity	NPD7799	Discontinued
0.6835	Remote Similarity	NPD2935	Discontinued
0.6832	Remote Similarity	NPD8131	Suspended
0.6815	Remote Similarity	NPD7097	Phase 1
0.6813	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.681	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD3021	Approved
0.6809	Remote Similarity	NPD3022	Approved
0.6802	Remote Similarity	NPD6232	Discontinued
0.6786	Remote Similarity	NPD2342	Discontinued
0.6786	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD6858	Approved
0.6783	Remote Similarity	NPD7094	Approved
0.678	Remote Similarity	NPD7240	Approved
0.6778	Remote Similarity	NPD8434	Phase 2
0.6776	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6233	Phase 2
0.6774	Remote Similarity	NPD7715	Approved
0.6774	Remote Similarity	NPD7714	Approved
0.6772	Remote Similarity	NPD8319	Approved
0.6772	Remote Similarity	NPD8320	Phase 1
0.677	Remote Similarity	NPD3750	Approved
0.6766	Remote Similarity	NPD6677	Suspended
0.6759	Remote Similarity	NPD4198	Discontinued
0.6755	Remote Similarity	NPD8651	Approved
0.6752	Remote Similarity	NPD6653	Approved
0.6746	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD6959	Discontinued
0.6738	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD2861	Phase 2
0.673	Remote Similarity	NPD4477	Approved
0.673	Remote Similarity	NPD2531	Phase 2
0.673	Remote Similarity	NPD4476	Approved
0.673	Remote Similarity	NPD6099	Approved
0.673	Remote Similarity	NPD6100	Approved
0.6723	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1164	Approved
0.6708	Remote Similarity	NPD3638	Discontinued
0.6707	Remote Similarity	NPD2534	Approved
0.6707	Remote Similarity	NPD2532	Approved
0.6707	Remote Similarity	NPD2533	Approved
0.6706	Remote Similarity	NPD7058	Phase 2
0.6706	Remote Similarity	NPD7057	Phase 3
0.6705	Remote Similarity	NPD7229	Phase 3
0.6705	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD9495	Approved
0.669	Remote Similarity	NPD4750	Phase 3
0.6689	Remote Similarity	NPD1651	Approved
0.6689	Remote Similarity	NPD5691	Approved
0.6689	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7266	Discontinued
0.6686	Remote Similarity	NPD4666	Phase 3
0.6685	Remote Similarity	NPD7685	Pre-registration
0.6667	Remote Similarity	NPD4956	Approved
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7610	Discontinued
0.6647	Remote Similarity	NPD3226	Approved
0.6646	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD5958	Discontinued
0.6646	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4534	Discontinued
0.6646	Remote Similarity	NPD4097	Suspended
0.6642	Remote Similarity	NPD3020	Approved
0.6632	Remote Similarity	NPD7435	Discontinued
0.6631	Remote Similarity	NPD7700	Phase 2
0.6631	Remote Similarity	NPD7699	Phase 2
0.6629	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6166	Phase 2
0.6629	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5709	Phase 3
0.6627	Remote Similarity	NPD7427	Discontinued
0.6627	Remote Similarity	NPD6801	Discontinued
0.6623	Remote Similarity	NPD1608	Approved
0.6621	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD5035	Approved
0.6609	Remote Similarity	NPD3787	Discontinued
0.6608	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6599	Discontinued
0.6607	Remote Similarity	NPD4380	Phase 2
0.6606	Remote Similarity	NPD3645	Discontinued
0.6605	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD6674	Discontinued
0.6603	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6765	Approved
0.6592	Remote Similarity	NPD6764	Approved
0.6592	Remote Similarity	NPD5039	Approved
0.6588	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD2346	Discontinued
0.6576	Remote Similarity	NPD2490	Approved
0.6576	Remote Similarity	NPD2488	Approved
0.6571	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7305	Phase 1
0.6562	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2799	Discontinued

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