NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	366.15
Volume:	371.782
LogP:	1.959
LogD:	1.945
LogS:	-5.106
# Rotatable Bonds:	3
TPSA:	75.99
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.817
Synthetic Accessibility Score:	4.157
Fsp3:	0.409
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:	-4.891
MDCK Permeability:	1.2354807040537708e-05
Pgp-inhibitor:	0.034
Pgp-substrate:	0.935
Human Intestinal Absorption (HIA):	0.067
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.836

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.159
Plasma Protein Binding (PPB):	82.59929656982422%
Volume Distribution (VD):	1.763
Pgp-substrate:	12.807952880859375%

ADMET: Metabolism

CYP1A2-inhibitor:	0.473
CYP1A2-substrate:	0.649
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.655
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.11
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.195
CYP3A4-inhibitor:	0.204
CYP3A4-substrate:	0.461

ADMET: Excretion

Clearance (CL):	2.313
Half-life (T1/2):	0.074

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.433
Drug-inuced Liver Injury (DILI):	0.954
AMES Toxicity:	0.864
Rat Oral Acute Toxicity:	0.924
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.207
Carcinogencity:	0.846
Eye Corrosion:	0.003
Eye Irritation:	0.019
Respiratory Toxicity:	0.904

Download Data

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

Natural Product: NPC478161

Natural Product ID:	NPC478161
*Common Name:**	Xestosaprol H
IUPAC Name:	(1S,16S,17R)-17-hydroxy-8-(2-hydroxyethoxy)-1-methyl-14-oxapentacyclo[11.6.1.02,11.04,9.016,20]icosa-2(11),3,5,7,9,13(20)-hexaen-12-one
Synonyms:	Xestosaprol H
Standard InCHIKey:	CMIANYWOWFNDPD-JIGPKXGUSA-N
Standard InCHI:	InChI=1S/C22H22O5/c1-22-6-5-17(24)15-11-27-21(19(15)22)20(25)14-10-13-12(9-16(14)22)3-2-4-18(13)26-8-7-23/h2-4,9-10,15,17,23-24H,5-8,11H2,1H3/t15-,17+,22-/m0/s1
SMILES:	C[C@@]12CC[C@H]([C@H]3C1=C(C(=O)C4=C2C=C5C=CC=C(C5=C4)OCCO)OC3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	46849022
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes 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
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908959]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Caledonian	n.a.	PMID[1453184]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Thai	n.a.	PMID[14640515]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	thai	n.a.	PMID[15217287]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[1710256]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Indonesia	n.a.	PMID[20503979]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	coral reef habitat at a depth of approximately 20 m from the sea bed surface, at Sangalaki, Indonesia (2 04 59 N, 118 23 41 E)	1996-MAR	PMID[20503979]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[31260310]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	Philippine	n.a.	PMID[7473578]
NPO32702	xestospongia sp.	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798966]

☑ 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
NPT740	Individual Protein	Beta-secretase 1	Homo sapiens	IC50	=	82000	nM	PMID[20503979]

☑ 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 NPC478161 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	377
0.1-0.2	1364
0.2-0.3	2805
0.3-0.4	6674
0.4-0.5	11284
0.5-0.6	5242
0.6-0.7	7187
0.7-0.8	7567
0.8-0.85	188
0.85-0.9	5
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC478159
0.9524	High Similarity	NPC478163
0.9128	High Similarity	NPC478160
0.8993	High Similarity	NPC478164
0.8671	High Similarity	NPC288353
0.8654	High Similarity	NPC306011
0.8654	High Similarity	NPC472838
0.8649	High Similarity	NPC471670
0.8591	High Similarity	NPC186647
0.859	High Similarity	NPC475718
0.8589	High Similarity	NPC263212
0.8581	High Similarity	NPC472839
0.8581	High Similarity	NPC474556
0.8562	High Similarity	NPC472836
0.8545	High Similarity	NPC313717
0.8545	High Similarity	NPC315306
0.8528	High Similarity	NPC41689
0.8481	Intermediate Similarity	NPC44606
0.8481	Intermediate Similarity	NPC27615
0.8477	Intermediate Similarity	NPC470407
0.8476	Intermediate Similarity	NPC255787
0.8471	Intermediate Similarity	NPC58310
0.8471	Intermediate Similarity	NPC295977
0.8462	Intermediate Similarity	NPC472841
0.8456	Intermediate Similarity	NPC22644
0.8447	Intermediate Similarity	NPC472299
0.8431	Intermediate Similarity	NPC201297
0.8402	Intermediate Similarity	NPC47191
0.8397	Intermediate Similarity	NPC469425
0.8397	Intermediate Similarity	NPC58373
0.8389	Intermediate Similarity	NPC23894
0.8385	Intermediate Similarity	NPC123153
0.8378	Intermediate Similarity	NPC183103
0.8375	Intermediate Similarity	NPC3898
0.8354	Intermediate Similarity	NPC308156
0.8344	Intermediate Similarity	NPC290601
0.8323	Intermediate Similarity	NPC308006
0.8323	Intermediate Similarity	NPC469507
0.8323	Intermediate Similarity	NPC478223
0.8323	Intermediate Similarity	NPC114513
0.8323	Intermediate Similarity	NPC245522
0.8313	Intermediate Similarity	NPC179170
0.8313	Intermediate Similarity	NPC88958
0.8311	Intermediate Similarity	NPC239134
0.8311	Intermediate Similarity	NPC164295
0.8303	Intermediate Similarity	NPC316262
0.8303	Intermediate Similarity	NPC314653
0.8302	Intermediate Similarity	NPC230848
0.8291	Intermediate Similarity	NPC472837
0.8284	Intermediate Similarity	NPC470667
0.8284	Intermediate Similarity	NPC186800
0.8282	Intermediate Similarity	NPC79571
0.8282	Intermediate Similarity	NPC472618
0.828	Intermediate Similarity	NPC478018
0.8272	Intermediate Similarity	NPC67197
0.8269	Intermediate Similarity	NPC478166
0.8253	Intermediate Similarity	NPC291742
0.8239	Intermediate Similarity	NPC140133
0.8232	Intermediate Similarity	NPC478134
0.8232	Intermediate Similarity	NPC316457
0.8228	Intermediate Similarity	NPC95526
0.8225	Intermediate Similarity	NPC154986
0.8221	Intermediate Similarity	NPC8389
0.8217	Intermediate Similarity	NPC286038
0.821	Intermediate Similarity	NPC7059
0.8205	Intermediate Similarity	NPC469385
0.8205	Intermediate Similarity	NPC196941
0.8205	Intermediate Similarity	NPC290038
0.8205	Intermediate Similarity	NPC309169
0.8204	Intermediate Similarity	NPC469521
0.8204	Intermediate Similarity	NPC150131
0.82	Intermediate Similarity	NPC78307
0.82	Intermediate Similarity	NPC470406
0.8199	Intermediate Similarity	NPC84721
0.8188	Intermediate Similarity	NPC279596
0.8187	Intermediate Similarity	NPC48671
0.8187	Intermediate Similarity	NPC294511
0.8187	Intermediate Similarity	NPC145830
0.8187	Intermediate Similarity	NPC121615
0.8182	Intermediate Similarity	NPC473499
0.8176	Intermediate Similarity	NPC472298
0.8176	Intermediate Similarity	NPC80370
0.8171	Intermediate Similarity	NPC472961
0.8171	Intermediate Similarity	NPC313368
0.8171	Intermediate Similarity	NPC472962
0.8171	Intermediate Similarity	NPC470810
0.8165	Intermediate Similarity	NPC52692
0.8165	Intermediate Similarity	NPC66991
0.8163	Intermediate Similarity	NPC478162
0.8163	Intermediate Similarity	NPC478165
0.816	Intermediate Similarity	NPC317900
0.816	Intermediate Similarity	NPC294300
0.816	Intermediate Similarity	NPC299094
0.816	Intermediate Similarity	NPC10051
0.816	Intermediate Similarity	NPC473282
0.816	Intermediate Similarity	NPC104380
0.816	Intermediate Similarity	NPC476404
0.816	Intermediate Similarity	NPC217602
0.8155	Intermediate Similarity	NPC473095
0.8155	Intermediate Similarity	NPC473096
0.8155	Intermediate Similarity	NPC472619
0.8153	Intermediate Similarity	NPC478019
0.8146	Intermediate Similarity	NPC474659
0.8141	Intermediate Similarity	NPC53016
0.8141	Intermediate Similarity	NPC158871
0.8137	Intermediate Similarity	NPC164912
0.8137	Intermediate Similarity	NPC282793
0.8137	Intermediate Similarity	NPC10429
0.8137	Intermediate Similarity	NPC87708
0.8137	Intermediate Similarity	NPC60211
0.8133	Intermediate Similarity	NPC469395
0.8133	Intermediate Similarity	NPC290160
0.8133	Intermediate Similarity	NPC476295
0.8121	Intermediate Similarity	NPC269117
0.8117	Intermediate Similarity	NPC477408
0.8113	Intermediate Similarity	NPC474107
0.811	Intermediate Similarity	NPC104876
0.811	Intermediate Similarity	NPC245891
0.811	Intermediate Similarity	NPC226287
0.8107	Intermediate Similarity	NPC313304
0.8107	Intermediate Similarity	NPC52598
0.8105	Intermediate Similarity	NPC475957
0.8101	Intermediate Similarity	NPC39361
0.8098	Intermediate Similarity	NPC208152
0.8098	Intermediate Similarity	NPC221992
0.8098	Intermediate Similarity	NPC78492
0.8098	Intermediate Similarity	NPC213401
0.8098	Intermediate Similarity	NPC194499
0.8095	Intermediate Similarity	NPC472660
0.8095	Intermediate Similarity	NPC473094
0.8095	Intermediate Similarity	NPC44602
0.8086	Intermediate Similarity	NPC303950
0.8086	Intermediate Similarity	NPC329844
0.8086	Intermediate Similarity	NPC469966
0.8084	Intermediate Similarity	NPC472784
0.8077	Intermediate Similarity	NPC192597
0.8077	Intermediate Similarity	NPC176030
0.8077	Intermediate Similarity	NPC69755
0.8077	Intermediate Similarity	NPC169214
0.8077	Intermediate Similarity	NPC141817
0.8077	Intermediate Similarity	NPC229218
0.8075	Intermediate Similarity	NPC232645
0.8075	Intermediate Similarity	NPC189773
0.8075	Intermediate Similarity	NPC471613
0.8075	Intermediate Similarity	NPC149526
0.8075	Intermediate Similarity	NPC72958
0.8075	Intermediate Similarity	NPC118427
0.8075	Intermediate Similarity	NPC474414
0.8075	Intermediate Similarity	NPC474417
0.8075	Intermediate Similarity	NPC144283
0.8072	Intermediate Similarity	NPC101116
0.8072	Intermediate Similarity	NPC212099
0.8072	Intermediate Similarity	NPC475106
0.8072	Intermediate Similarity	NPC216752
0.8072	Intermediate Similarity	NPC146837
0.8072	Intermediate Similarity	NPC278329
0.8063	Intermediate Similarity	NPC228842
0.8061	Intermediate Similarity	NPC284495
0.8061	Intermediate Similarity	NPC469840
0.8059	Intermediate Similarity	NPC472639
0.8059	Intermediate Similarity	NPC472638
0.8059	Intermediate Similarity	NPC118128
0.8059	Intermediate Similarity	NPC472620
0.8059	Intermediate Similarity	NPC473113
0.8049	Intermediate Similarity	NPC272196
0.8049	Intermediate Similarity	NPC472823
0.8046	Intermediate Similarity	NPC478001
0.8046	Intermediate Similarity	NPC228209
0.8039	Intermediate Similarity	NPC232996
0.8038	Intermediate Similarity	NPC225351
0.8038	Intermediate Similarity	NPC170055
0.8037	Intermediate Similarity	NPC180901
0.8037	Intermediate Similarity	NPC300757
0.8036	Intermediate Similarity	NPC178173
0.8036	Intermediate Similarity	NPC120857
0.8036	Intermediate Similarity	NPC191012
0.8036	Intermediate Similarity	NPC85047
0.8036	Intermediate Similarity	NPC17274
0.8035	Intermediate Similarity	NPC244903
0.8025	Intermediate Similarity	NPC471349
0.8025	Intermediate Similarity	NPC216035
0.8025	Intermediate Similarity	NPC217149
0.8025	Intermediate Similarity	NPC471347
0.8025	Intermediate Similarity	NPC171651
0.8025	Intermediate Similarity	NPC35567
0.8025	Intermediate Similarity	NPC243171
0.8025	Intermediate Similarity	NPC472840
0.8025	Intermediate Similarity	NPC40356
0.8025	Intermediate Similarity	NPC154683
0.8025	Intermediate Similarity	NPC163948
0.8024	Intermediate Similarity	NPC100849
0.8024	Intermediate Similarity	NPC277618
0.8024	Intermediate Similarity	NPC475779
0.8023	Intermediate Similarity	NPC312630
0.8023	Intermediate Similarity	NPC324220
0.8013	Intermediate Similarity	NPC312560
0.8013	Intermediate Similarity	NPC263337
0.8012	Intermediate Similarity	NPC85368
0.8012	Intermediate Similarity	NPC472906
0.8012	Intermediate Similarity	NPC469393

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 NPC478161 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	863
0.2-0.3	1427
0.3-0.4	2458
0.4-0.5	2150
0.5-0.6	1197
0.6-0.7	557
0.7-0.8	180
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8291	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6273	Approved
0.8129	Intermediate Similarity	NPD4628	Phase 3
0.8063	Intermediate Similarity	NPD7458	Discontinued
0.8047	Intermediate Similarity	NPD5844	Phase 1
0.8038	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD7003	Approved
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.7975	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD6355	Discontinued
0.7831	Intermediate Similarity	NPD7075	Discontinued
0.7821	Intermediate Similarity	NPD2346	Discontinued
0.7805	Intermediate Similarity	NPD6801	Discontinued
0.7798	Intermediate Similarity	NPD6959	Discontinued
0.7778	Intermediate Similarity	NPD4060	Phase 1
0.7763	Intermediate Similarity	NPD6798	Discontinued
0.7758	Intermediate Similarity	NPD7819	Suspended
0.7722	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7709	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7236	Approved
0.7684	Intermediate Similarity	NPD8434	Phase 2
0.7683	Intermediate Similarity	NPD4380	Phase 2
0.7674	Intermediate Similarity	NPD3751	Discontinued
0.7665	Intermediate Similarity	NPD3882	Suspended
0.7661	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6166	Phase 2
0.7661	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD6799	Approved
0.7633	Intermediate Similarity	NPD5494	Approved
0.7622	Intermediate Similarity	NPD3226	Approved
0.7614	Intermediate Similarity	NPD8312	Approved
0.7614	Intermediate Similarity	NPD8313	Approved
0.7605	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD5762	Approved
0.7595	Intermediate Similarity	NPD1471	Phase 3
0.7595	Intermediate Similarity	NPD5763	Approved
0.7593	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3972	Approved
0.7582	Intermediate Similarity	NPD7095	Approved
0.758	Intermediate Similarity	NPD2799	Discontinued
0.7561	Intermediate Similarity	NPD7239	Suspended
0.7544	Intermediate Similarity	NPD3787	Discontinued
0.7532	Intermediate Similarity	NPD2438	Suspended
0.7529	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7473	Discontinued
0.75	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD6764	Approved
0.75	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6765	Approved
0.75	Intermediate Similarity	NPD5403	Approved
0.7486	Intermediate Similarity	NPD8150	Discontinued
0.7485	Intermediate Similarity	NPD1934	Approved
0.7485	Intermediate Similarity	NPD5401	Approved
0.7485	Intermediate Similarity	NPD8127	Discontinued
0.7484	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6233	Phase 2
0.7483	Intermediate Similarity	NPD1283	Approved
0.7471	Intermediate Similarity	NPD7177	Discontinued
0.7456	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3750	Approved
0.7442	Intermediate Similarity	NPD6232	Discontinued
0.7436	Intermediate Similarity	NPD4140	Approved
0.7432	Intermediate Similarity	NPD1651	Approved
0.7425	Intermediate Similarity	NPD7411	Suspended
0.7421	Intermediate Similarity	NPD6100	Approved
0.7421	Intermediate Similarity	NPD6099	Approved
0.7421	Intermediate Similarity	NPD2796	Approved
0.7412	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5735	Approved
0.7378	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2344	Approved
0.7372	Intermediate Similarity	NPD8032	Phase 2
0.7358	Intermediate Similarity	NPD3748	Approved
0.7355	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD8166	Discontinued
0.7345	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6797	Phase 2
0.734	Intermediate Similarity	NPD3057	Approved
0.7333	Intermediate Similarity	NPD6784	Approved
0.7333	Intermediate Similarity	NPD6785	Approved
0.7333	Intermediate Similarity	NPD5049	Phase 3
0.7333	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1549	Phase 2
0.7326	Intermediate Similarity	NPD6779	Approved
0.7326	Intermediate Similarity	NPD6780	Approved
0.7326	Intermediate Similarity	NPD6777	Approved
0.7326	Intermediate Similarity	NPD6781	Approved
0.7326	Intermediate Similarity	NPD6778	Approved
0.7326	Intermediate Similarity	NPD6782	Approved
0.7326	Intermediate Similarity	NPD6776	Approved
0.7325	Intermediate Similarity	NPD2979	Phase 3
0.7312	Intermediate Similarity	NPD2935	Discontinued
0.7308	Intermediate Similarity	NPD3268	Approved
0.7308	Intermediate Similarity	NPD2313	Discontinued
0.7305	Intermediate Similarity	NPD2649	Approved
0.7305	Intermediate Similarity	NPD2651	Approved
0.7303	Intermediate Similarity	NPD7251	Discontinued
0.7302	Intermediate Similarity	NPD7435	Discontinued
0.7301	Intermediate Similarity	NPD3887	Approved
0.7301	Intermediate Similarity	NPD2354	Approved
0.7285	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD1281	Approved
0.7284	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7199	Phase 2
0.7273	Intermediate Similarity	NPD3818	Discontinued
0.7273	Intermediate Similarity	NPD2798	Approved
0.7267	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD919	Approved
0.7263	Intermediate Similarity	NPD7808	Phase 3
0.7257	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1876	Approved
0.7251	Intermediate Similarity	NPD7768	Phase 2
0.725	Intermediate Similarity	NPD4308	Phase 3
0.7249	Intermediate Similarity	NPD3533	Approved
0.7249	Intermediate Similarity	NPD2972	Approved
0.7239	Intermediate Similarity	NPD4110	Phase 3
0.7239	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD5761	Phase 2
0.7235	Intermediate Similarity	NPD5760	Phase 2
0.7235	Intermediate Similarity	NPD8455	Phase 2
0.7235	Intermediate Similarity	NPD2801	Approved
0.7229	Intermediate Similarity	NPD1512	Approved
0.7222	Intermediate Similarity	NPD2897	Discontinued
0.7222	Intermediate Similarity	NPD4534	Discontinued
0.7222	Intermediate Similarity	NPD2424	Discontinued
0.7222	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3749	Approved
0.7208	Intermediate Similarity	NPD2797	Approved
0.7195	Intermediate Similarity	NPD2309	Approved
0.7191	Intermediate Similarity	NPD7074	Phase 3
0.719	Intermediate Similarity	NPD5327	Phase 3
0.7184	Intermediate Similarity	NPD1247	Approved
0.7178	Intermediate Similarity	NPD6674	Discontinued
0.7174	Intermediate Similarity	NPD2488	Approved
0.7174	Intermediate Similarity	NPD2490	Approved
0.7169	Intermediate Similarity	NPD2532	Approved
0.7169	Intermediate Similarity	NPD2534	Approved
0.7169	Intermediate Similarity	NPD2533	Approved
0.7167	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7028	Phase 2
0.7158	Intermediate Similarity	NPD2491	Approved
0.7152	Intermediate Similarity	NPD4062	Phase 3
0.7151	Intermediate Similarity	NPD7058	Phase 2
0.7151	Intermediate Similarity	NPD7057	Phase 3
0.7143	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7229	Phase 3
0.7143	Intermediate Similarity	NPD1510	Phase 2
0.7135	Intermediate Similarity	NPD1465	Phase 2
0.7135	Intermediate Similarity	NPD7054	Approved
0.7134	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7008	Discontinued
0.7125	Intermediate Similarity	NPD1607	Approved
0.7124	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD7697	Approved
0.712	Intermediate Similarity	NPD7698	Approved
0.712	Intermediate Similarity	NPD7696	Phase 3
0.7117	Intermediate Similarity	NPD5958	Discontinued
0.7108	Intermediate Similarity	NPD1511	Approved
0.7108	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7390	Discontinued
0.7107	Intermediate Similarity	NPD4307	Phase 2
0.7107	Intermediate Similarity	NPD3620	Phase 2
0.7107	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD3926	Phase 2
0.7099	Intermediate Similarity	NPD4476	Approved
0.7099	Intermediate Similarity	NPD5405	Approved
0.7099	Intermediate Similarity	NPD2531	Phase 2
0.7099	Intermediate Similarity	NPD5408	Approved
0.7099	Intermediate Similarity	NPD5406	Approved
0.7099	Intermediate Similarity	NPD4477	Approved
0.7099	Intermediate Similarity	NPD5404	Approved
0.7097	Intermediate Similarity	NPD3266	Approved
0.7097	Intermediate Similarity	NPD3267	Approved
0.7095	Intermediate Similarity	NPD7472	Approved
0.7086	Intermediate Similarity	NPD5691	Approved
0.7083	Intermediate Similarity	NPD7871	Phase 2
0.7083	Intermediate Similarity	NPD7870	Phase 2
0.7079	Intermediate Similarity	NPD7799	Discontinued
0.7079	Intermediate Similarity	NPD2163	Approved
0.7077	Intermediate Similarity	NPD7874	Approved
0.7077	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD37	Approved
0.7076	Intermediate Similarity	NPD6844	Discontinued
0.7073	Intermediate Similarity	NPD2800	Approved
0.707	Intermediate Similarity	NPD6832	Phase 2
0.7069	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD3448	Approved
0.7066	Intermediate Similarity	NPD4661	Approved
0.7066	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4662	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