NPASS Compound

Structure

NPC473456 OpenBabel07101718322D 31 35 0 0 1 0 0 0 0 0999 V2000 4.0715 0.0518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8550 2.2306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4716 -2.5730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3586 -0.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4357 -1.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5696 -2.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 1.2930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 -1.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3586 0.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5075 -0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 0.7930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 -2.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5696 -0.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 -0.2070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6369 -0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7036 -0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4357 -0.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7036 -1.7070 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2395 -0.7070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3735 0.7930 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9716 -0.7070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0576 0.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1055 -0.2070 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5075 1.2930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9716 -1.7070 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3735 -0.2070 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3017 -0.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 -2.2070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9885 1.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9716 -1.7070 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 9 1 0 0 0 0 4 10 1 0 0 0 0 5 6 2 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 11 1 0 0 0 0 7 20 1 0 0 0 0 8 12 1 0 0 0 0 8 19 1 0 0 0 0 9 24 1 0 0 0 0 11 23 1 0 0 0 0 12 25 1 0 0 0 0 13 16 2 0 0 0 0 13 17 1 0 0 0 0 14 16 1 0 0 0 0 14 21 1 0 0 0 0 15 26 1 0 0 0 0 15 31 1 0 0 0 0 16 18 1 0 0 0 0 17 27 2 0 0 0 0 18 28 2 0 0 0 0 19 23 1 6 0 0 0 19 26 1 0 0 0 0 20 24 1 6 0 0 0 20 26 1 0 0 0 0 21 23 1 6 0 0 0 21 25 1 0 0 0 0 22 24 1 0 0 0 0 22 29 2 0 0 0 0 22 31 1 0 0 0 0 23 1 1 6 0 0 0 24 2 1 6 0 0 0 25 3 1 6 0 0 0 25 30 1 0 0 0 0 26 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.24
Volume:	446.239
LogP:	3.965
LogD:	3.328
LogS:	-4.189
# Rotatable Bonds:	1
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	5.467
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.251
MDCK Permeability:	2.207385841757059e-05
Pgp-inhibitor:	0.028
Pgp-substrate:	0.509
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.046
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.444
Plasma Protein Binding (PPB):	96.15703582763672%
Volume Distribution (VD):	1.047
Pgp-substrate:	4.770769119262695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.423
CYP2C9-inhibitor:	0.134
CYP2C9-substrate:	0.44
CYP2D6-inhibitor:	0.276
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.953
CYP3A4-substrate:	0.687

ADMET: Excretion

Clearance (CL):	17.305
Half-life (T1/2):	0.614

ADMET: Toxicity

hERG Blockers:	0.258
Human Hepatotoxicity (H-HT):	0.579
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.187
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.574
Carcinogencity:	0.792
Eye Corrosion:	0.006
Eye Irritation:	0.329
Respiratory Toxicity:	0.953

Download Data

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

Natural Product: NPC473456

Natural Product ID:	NPC473456
*Common Name:**	VKVSSUJFHYCONL-VRRJBYJJSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VKVSSUJFHYCONL-VRRJBYJJSA-N
Standard InCHI:	InChI=1S/C26H34O5/c1-23-11-7-20-24(2)9-4-10-26(20,15-31-22(24)29)19(23)8-12-25(3,30)21(23)14-16-13-17(27)5-6-18(16)28/h5-6,13,19-21,30H,4,7-12,14-15H2,1-3H3/t19-,20-,21-,23+,24-,25-,26-/m0/s1
SMILES:	O=C1C=CC(=O)C(=C1)C[C@@H]1[C@@](C)(O)CC[C@H]2[C@@]1(C)CC[C@@H]1[C@@]32CCC[C@]1(C)C(=O)OC3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL437547
PubChem CID:	11464470
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350165]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	Okinawan, Japan	n.a.	PMID[14695804]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332859]
NPO33317	strongylophora	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15332859]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17407351]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[25987373]
NPO24364	Petrosia corticata	Species	Petrosiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[7807132]
NPO33317	strongylophora	n.a.	n.a.	n.a.	n.a.	Philippine	n.a.	PMID[9677282]
NPO24364	Petrosia corticata	Species	Petrosiidae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	7.0	ug.mL-1	PMID[507069]

☑ 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 NPC473456 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	219
0.1-0.2	1313
0.2-0.3	4703
0.3-0.4	10352
0.4-0.5	12074
0.5-0.6	6454
0.6-0.7	4855
0.7-0.8	2287
0.8-0.85	267
0.85-0.9	157
0.9-0.95	15
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9271	High Similarity	NPC179208
0.9032	High Similarity	NPC74751
0.9	High Similarity	NPC30421
0.8936	High Similarity	NPC139570
0.8925	High Similarity	NPC295643
0.8925	High Similarity	NPC272075
0.8925	High Similarity	NPC214756
0.8817	High Similarity	NPC4036
0.8817	High Similarity	NPC233455
0.8817	High Similarity	NPC145067
0.8817	High Similarity	NPC65120
0.8817	High Similarity	NPC158030
0.875	High Similarity	NPC170131
0.875	High Similarity	NPC26413
0.8737	High Similarity	NPC274417
0.871	High Similarity	NPC113989
0.871	High Similarity	NPC328141
0.871	High Similarity	NPC474728
0.871	High Similarity	NPC120840
0.8687	High Similarity	NPC282233
0.8687	High Similarity	NPC95585
0.866	High Similarity	NPC471966
0.8646	High Similarity	NPC98874
0.8632	High Similarity	NPC474963
0.8632	High Similarity	NPC269729
0.8632	High Similarity	NPC474529
0.8617	High Similarity	NPC77099
0.8617	High Similarity	NPC60755
0.8617	High Similarity	NPC470590
0.8617	High Similarity	NPC285184
0.8602	High Similarity	NPC30522
0.8571	High Similarity	NPC474537
0.8542	High Similarity	NPC148523
0.8526	High Similarity	NPC86368
0.8526	High Similarity	NPC79117
0.8511	High Similarity	NPC291028
0.85	High Similarity	NPC478057
0.8495	Intermediate Similarity	NPC246708
0.8495	Intermediate Similarity	NPC40552
0.8495	Intermediate Similarity	NPC182797
0.8495	Intermediate Similarity	NPC52169
0.8478	Intermediate Similarity	NPC73038
0.8469	Intermediate Similarity	NPC478056
0.8469	Intermediate Similarity	NPC260149
0.8469	Intermediate Similarity	NPC58942
0.8462	Intermediate Similarity	NPC96095
0.8454	Intermediate Similarity	NPC327179
0.8454	Intermediate Similarity	NPC471039
0.8447	Intermediate Similarity	NPC41405
0.8438	Intermediate Similarity	NPC471207
0.8438	Intermediate Similarity	NPC184006
0.8438	Intermediate Similarity	NPC296164
0.8438	Intermediate Similarity	NPC23621
0.8438	Intermediate Similarity	NPC471040
0.8438	Intermediate Similarity	NPC78580
0.8421	Intermediate Similarity	NPC105189
0.8421	Intermediate Similarity	NPC230064
0.8421	Intermediate Similarity	NPC474525
0.8421	Intermediate Similarity	NPC218301
0.8404	Intermediate Similarity	NPC61543
0.8404	Intermediate Similarity	NPC293048
0.8404	Intermediate Similarity	NPC234346
0.8404	Intermediate Similarity	NPC25906
0.8404	Intermediate Similarity	NPC143232
0.8404	Intermediate Similarity	NPC198664
0.8404	Intermediate Similarity	NPC270768
0.8404	Intermediate Similarity	NPC477973
0.8404	Intermediate Similarity	NPC474700
0.8404	Intermediate Similarity	NPC130520
0.8404	Intermediate Similarity	NPC274330
0.8404	Intermediate Similarity	NPC59263
0.8404	Intermediate Similarity	NPC121798
0.8404	Intermediate Similarity	NPC290972
0.8404	Intermediate Similarity	NPC263393
0.8404	Intermediate Similarity	NPC64872
0.8404	Intermediate Similarity	NPC225585
0.8404	Intermediate Similarity	NPC127689
0.8404	Intermediate Similarity	NPC470588
0.84	Intermediate Similarity	NPC40918
0.8387	Intermediate Similarity	NPC68160
0.8387	Intermediate Similarity	NPC293564
0.8387	Intermediate Similarity	NPC98442
0.8387	Intermediate Similarity	NPC88716
0.8387	Intermediate Similarity	NPC46912
0.8387	Intermediate Similarity	NPC130577
0.8387	Intermediate Similarity	NPC142415
0.8387	Intermediate Similarity	NPC51700
0.8387	Intermediate Similarity	NPC307426
0.8387	Intermediate Similarity	NPC102683
0.8387	Intermediate Similarity	NPC162107
0.8387	Intermediate Similarity	NPC242468
0.8387	Intermediate Similarity	NPC476932
0.8387	Intermediate Similarity	NPC171203
0.8387	Intermediate Similarity	NPC18064
0.8384	Intermediate Similarity	NPC475202
0.8384	Intermediate Similarity	NPC475392
0.8384	Intermediate Similarity	NPC475385
0.8384	Intermediate Similarity	NPC472972
0.8367	Intermediate Similarity	NPC158347
0.8367	Intermediate Similarity	NPC89225
0.8351	Intermediate Similarity	NPC195715
0.8351	Intermediate Similarity	NPC23241
0.8351	Intermediate Similarity	NPC474727
0.8351	Intermediate Similarity	NPC147232
0.8351	Intermediate Similarity	NPC473240
0.8333	Intermediate Similarity	NPC474436
0.8333	Intermediate Similarity	NPC476416
0.8333	Intermediate Similarity	NPC275809
0.8333	Intermediate Similarity	NPC158059
0.8333	Intermediate Similarity	NPC307335
0.8333	Intermediate Similarity	NPC278459
0.8333	Intermediate Similarity	NPC471898
0.8333	Intermediate Similarity	NPC136313
0.8333	Intermediate Similarity	NPC49776
0.8333	Intermediate Similarity	NPC63118
0.8333	Intermediate Similarity	NPC118490
0.8333	Intermediate Similarity	NPC74855
0.8333	Intermediate Similarity	NPC202728
0.8333	Intermediate Similarity	NPC473217
0.8333	Intermediate Similarity	NPC118519
0.8317	Intermediate Similarity	NPC264048
0.8317	Intermediate Similarity	NPC90177
0.8317	Intermediate Similarity	NPC476889
0.8317	Intermediate Similarity	NPC95899
0.8317	Intermediate Similarity	NPC275583
0.8316	Intermediate Similarity	NPC470589
0.8316	Intermediate Similarity	NPC227467
0.8316	Intermediate Similarity	NPC126369
0.8316	Intermediate Similarity	NPC193750
0.8316	Intermediate Similarity	NPC111110
0.8316	Intermediate Similarity	NPC210037
0.8316	Intermediate Similarity	NPC477872
0.8316	Intermediate Similarity	NPC273621
0.8316	Intermediate Similarity	NPC18872
0.8316	Intermediate Similarity	NPC7260
0.8316	Intermediate Similarity	NPC120968
0.8316	Intermediate Similarity	NPC130278
0.8316	Intermediate Similarity	NPC290614
0.8316	Intermediate Similarity	NPC46441
0.83	Intermediate Similarity	NPC476888
0.83	Intermediate Similarity	NPC93744
0.8298	Intermediate Similarity	NPC470629
0.8298	Intermediate Similarity	NPC290690
0.8298	Intermediate Similarity	NPC181225
0.8298	Intermediate Similarity	NPC474512
0.8298	Intermediate Similarity	NPC473242
0.8298	Intermediate Similarity	NPC48107
0.8298	Intermediate Similarity	NPC17733
0.8298	Intermediate Similarity	NPC474925
0.8283	Intermediate Similarity	NPC114274
0.8283	Intermediate Similarity	NPC475876
0.828	Intermediate Similarity	NPC324063
0.828	Intermediate Similarity	NPC329943
0.828	Intermediate Similarity	NPC10005
0.828	Intermediate Similarity	NPC9892
0.828	Intermediate Similarity	NPC72638
0.828	Intermediate Similarity	NPC91525
0.828	Intermediate Similarity	NPC325594
0.8269	Intermediate Similarity	NPC310546
0.8265	Intermediate Similarity	NPC469545
0.8265	Intermediate Similarity	NPC476327
0.8265	Intermediate Similarity	NPC5532
0.8265	Intermediate Similarity	NPC62516
0.8265	Intermediate Similarity	NPC472806
0.8265	Intermediate Similarity	NPC167193
0.8265	Intermediate Similarity	NPC111684
0.8265	Intermediate Similarity	NPC473158
0.8265	Intermediate Similarity	NPC58052
0.8265	Intermediate Similarity	NPC61369
0.8265	Intermediate Similarity	NPC230151
0.8265	Intermediate Similarity	NPC476318
0.8265	Intermediate Similarity	NPC157113
0.8261	Intermediate Similarity	NPC156981
0.8252	Intermediate Similarity	NPC44063
0.8247	Intermediate Similarity	NPC148964
0.8247	Intermediate Similarity	NPC6818
0.8247	Intermediate Similarity	NPC476415
0.8247	Intermediate Similarity	NPC191412
0.8247	Intermediate Similarity	NPC23170
0.8247	Intermediate Similarity	NPC91010
0.8247	Intermediate Similarity	NPC60692
0.8247	Intermediate Similarity	NPC80365
0.8247	Intermediate Similarity	NPC114159
0.8241	Intermediate Similarity	NPC476965
0.8241	Intermediate Similarity	NPC470959
0.8235	Intermediate Similarity	NPC213366
0.8229	Intermediate Similarity	NPC966
0.8229	Intermediate Similarity	NPC228784
0.8229	Intermediate Similarity	NPC187722
0.8229	Intermediate Similarity	NPC300351
0.8229	Intermediate Similarity	NPC301244
0.8229	Intermediate Similarity	NPC235884
0.8229	Intermediate Similarity	NPC155120
0.8229	Intermediate Similarity	NPC471588
0.8229	Intermediate Similarity	NPC306541
0.8229	Intermediate Similarity	NPC52021
0.8229	Intermediate Similarity	NPC472975
0.8229	Intermediate Similarity	NPC25299
0.8229	Intermediate Similarity	NPC6255
0.8229	Intermediate Similarity	NPC71074

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 NPC473456 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	1592
0.2-0.3	3759
0.3-0.4	2330
0.4-0.5	804
0.5-0.6	213
0.6-0.7	154
0.7-0.8	97
0.8-0.85	0
0.85-0.9	4
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9032	High Similarity	NPD7748	Approved
0.9	High Similarity	NPD3573	Approved
0.8817	High Similarity	NPD7515	Phase 2
0.875	High Similarity	NPD7902	Approved
0.8438	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD7900	Approved
0.835	Intermediate Similarity	NPD6899	Approved
0.835	Intermediate Similarity	NPD6881	Approved
0.8252	Intermediate Similarity	NPD5697	Approved
0.8229	Intermediate Similarity	NPD6079	Approved
0.819	Intermediate Similarity	NPD7290	Approved
0.819	Intermediate Similarity	NPD7102	Approved
0.819	Intermediate Similarity	NPD6883	Approved
0.8173	Intermediate Similarity	NPD6011	Approved
0.8155	Intermediate Similarity	NPD6675	Approved
0.8155	Intermediate Similarity	NPD7128	Approved
0.8155	Intermediate Similarity	NPD6402	Approved
0.8155	Intermediate Similarity	NPD5739	Approved
0.8113	Intermediate Similarity	NPD6869	Approved
0.8113	Intermediate Similarity	NPD6649	Approved
0.8113	Intermediate Similarity	NPD6847	Approved
0.8113	Intermediate Similarity	NPD6617	Approved
0.8113	Intermediate Similarity	NPD6650	Approved
0.8113	Intermediate Similarity	NPD8130	Phase 1
0.8095	Intermediate Similarity	NPD6013	Approved
0.8095	Intermediate Similarity	NPD6014	Approved
0.8095	Intermediate Similarity	NPD6012	Approved
0.8037	Intermediate Similarity	NPD6882	Approved
0.8037	Intermediate Similarity	NPD8297	Approved
0.8021	Intermediate Similarity	NPD5328	Approved
0.8	Intermediate Similarity	NPD7320	Approved
0.7925	Intermediate Similarity	NPD6372	Approved
0.7925	Intermediate Similarity	NPD6373	Approved
0.7917	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5701	Approved
0.79	Intermediate Similarity	NPD5222	Approved
0.79	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD5221	Approved
0.7843	Intermediate Similarity	NPD5285	Approved
0.7843	Intermediate Similarity	NPD5286	Approved
0.7843	Intermediate Similarity	NPD4696	Approved
0.7835	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD6083	Phase 2
0.7822	Intermediate Similarity	NPD6084	Phase 2
0.7822	Intermediate Similarity	NPD5173	Approved
0.7778	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6399	Phase 3
0.7767	Intermediate Similarity	NPD5223	Approved
0.7732	Intermediate Similarity	NPD6672	Approved
0.7732	Intermediate Similarity	NPD5737	Approved
0.7723	Intermediate Similarity	NPD7614	Phase 1
0.7708	Intermediate Similarity	NPD7334	Approved
0.7708	Intermediate Similarity	NPD3618	Phase 1
0.7708	Intermediate Similarity	NPD7521	Approved
0.7708	Intermediate Similarity	NPD6409	Approved
0.7708	Intermediate Similarity	NPD5330	Approved
0.7708	Intermediate Similarity	NPD7146	Approved
0.7708	Intermediate Similarity	NPD6684	Approved
0.7692	Intermediate Similarity	NPD5224	Approved
0.7692	Intermediate Similarity	NPD4633	Approved
0.7692	Intermediate Similarity	NPD5225	Approved
0.7692	Intermediate Similarity	NPD5211	Phase 2
0.7692	Intermediate Similarity	NPD5226	Approved
0.7679	Intermediate Similarity	NPD6335	Approved
0.7677	Intermediate Similarity	NPD6411	Approved
0.7658	Intermediate Similarity	NPD6868	Approved
0.7647	Intermediate Similarity	NPD4755	Approved
0.7636	Intermediate Similarity	NPD4632	Approved
0.7624	Intermediate Similarity	NPD5695	Phase 3
0.7624	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5175	Approved
0.7619	Intermediate Similarity	NPD5174	Approved
0.7611	Intermediate Similarity	NPD7100	Approved
0.7611	Intermediate Similarity	NPD7101	Approved
0.7589	Intermediate Similarity	NPD7115	Discovery
0.7589	Intermediate Similarity	NPD6317	Approved
0.7573	Intermediate Similarity	NPD7638	Approved
0.7573	Intermediate Similarity	NPD5696	Approved
0.7551	Intermediate Similarity	NPD6903	Approved
0.7549	Intermediate Similarity	NPD7732	Phase 3
0.7549	Intermediate Similarity	NPD4697	Phase 3
0.7547	Intermediate Similarity	NPD5141	Approved
0.7526	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD6313	Approved
0.7522	Intermediate Similarity	NPD6314	Approved
0.75	Intermediate Similarity	NPD4700	Approved
0.75	Intermediate Similarity	NPD8328	Phase 3
0.75	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD8034	Phase 2
0.75	Intermediate Similarity	NPD6274	Approved
0.75	Intermediate Similarity	NPD7639	Approved
0.75	Intermediate Similarity	NPD7640	Approved
0.7477	Intermediate Similarity	NPD6008	Approved
0.7475	Intermediate Similarity	NPD6080	Approved
0.7475	Intermediate Similarity	NPD6101	Approved
0.7475	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD6673	Approved
0.7475	Intermediate Similarity	NPD6904	Approved
0.7447	Intermediate Similarity	NPD4695	Discontinued
0.7434	Intermediate Similarity	NPD6009	Approved
0.7426	Intermediate Similarity	NPD4202	Approved
0.7423	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD7736	Approved
0.7391	Intermediate Similarity	NPD6319	Approved
0.735	Intermediate Similarity	NPD7604	Phase 2
0.734	Intermediate Similarity	NPD7645	Phase 2
0.7339	Intermediate Similarity	NPD4729	Approved
0.7339	Intermediate Similarity	NPD4730	Approved
0.7328	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD5983	Phase 2
0.7327	Intermediate Similarity	NPD5281	Approved
0.7327	Intermediate Similarity	NPD5284	Approved
0.732	Intermediate Similarity	NPD3665	Phase 1
0.732	Intermediate Similarity	NPD4786	Approved
0.732	Intermediate Similarity	NPD3133	Approved
0.732	Intermediate Similarity	NPD3666	Approved
0.73	Intermediate Similarity	NPD4753	Phase 2
0.7292	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4221	Approved
0.7292	Intermediate Similarity	NPD3667	Approved
0.7292	Intermediate Similarity	NPD4223	Phase 3
0.729	Intermediate Similarity	NPD4754	Approved
0.7288	Intermediate Similarity	NPD7492	Approved
0.7282	Intermediate Similarity	NPD5210	Approved
0.7282	Intermediate Similarity	NPD4629	Approved
0.7245	Intermediate Similarity	NPD1694	Approved
0.7245	Intermediate Similarity	NPD5329	Approved
0.7241	Intermediate Similarity	NPD6054	Approved
0.7227	Intermediate Similarity	NPD6336	Discontinued
0.7227	Intermediate Similarity	NPD6616	Approved
0.7207	Intermediate Similarity	NPD5251	Approved
0.7207	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5249	Phase 3
0.7207	Intermediate Similarity	NPD5135	Approved
0.7207	Intermediate Similarity	NPD4634	Approved
0.7207	Intermediate Similarity	NPD5247	Approved
0.7207	Intermediate Similarity	NPD5250	Approved
0.7207	Intermediate Similarity	NPD5169	Approved
0.7207	Intermediate Similarity	NPD5248	Approved
0.72	Intermediate Similarity	NPD5208	Approved
0.7184	Intermediate Similarity	NPD6001	Approved
0.7182	Intermediate Similarity	NPD5168	Approved
0.7182	Intermediate Similarity	NPD5128	Approved
0.7179	Intermediate Similarity	NPD6908	Approved
0.7179	Intermediate Similarity	NPD6909	Approved
0.7172	Intermediate Similarity	NPD5690	Phase 2
0.7172	Intermediate Similarity	NPD6098	Approved
0.7172	Intermediate Similarity	NPD4623	Approved
0.7172	Intermediate Similarity	NPD4519	Discontinued
0.7167	Intermediate Similarity	NPD7078	Approved
0.7157	Intermediate Similarity	NPD6050	Approved
0.7157	Intermediate Similarity	NPD5693	Phase 1
0.7157	Intermediate Similarity	NPD5694	Approved
0.7156	Intermediate Similarity	NPD4767	Approved
0.7156	Intermediate Similarity	NPD4768	Approved
0.7143	Intermediate Similarity	NPD4197	Approved
0.7143	Intermediate Similarity	NPD5215	Approved
0.7143	Intermediate Similarity	NPD5127	Approved
0.7143	Intermediate Similarity	NPD5216	Approved
0.7143	Intermediate Similarity	NPD5217	Approved
0.7119	Intermediate Similarity	NPD6370	Approved
0.7117	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD6412	Phase 2
0.7083	Intermediate Similarity	NPD7507	Approved
0.7059	Intermediate Similarity	NPD5207	Approved
0.7059	Intermediate Similarity	NPD5692	Phase 3
0.7041	Intermediate Similarity	NPD4788	Approved
0.7034	Intermediate Similarity	NPD6016	Approved
0.7034	Intermediate Similarity	NPD6015	Approved
0.7027	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4138	Approved
0.7	Intermediate Similarity	NPD5205	Approved
0.7	Intermediate Similarity	NPD4688	Approved
0.7	Intermediate Similarity	NPD4689	Approved
0.7	Intermediate Similarity	NPD4693	Phase 3
0.7	Intermediate Similarity	NPD4690	Approved
0.6983	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4195	Approved
0.6975	Remote Similarity	NPD5988	Approved
0.697	Remote Similarity	NPD3668	Phase 3
0.6957	Remote Similarity	NPD5167	Approved
0.6949	Remote Similarity	NPD6059	Approved
0.6923	Remote Similarity	NPD5778	Approved
0.6923	Remote Similarity	NPD5779	Approved
0.6916	Remote Similarity	NPD4225	Approved
0.6911	Remote Similarity	NPD7319	Approved
0.6907	Remote Similarity	NPD7525	Registered
0.6885	Remote Similarity	NPD8293	Discontinued
0.6881	Remote Similarity	NPD7632	Discontinued
0.6875	Remote Similarity	NPD3617	Approved
0.6875	Remote Similarity	NPD6686	Approved
0.6832	Remote Similarity	NPD5279	Phase 3
0.6832	Remote Similarity	NPD4694	Approved
0.6832	Remote Similarity	NPD5280	Approved
0.6814	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6614	Approved
0.6778	Remote Similarity	NPD7331	Phase 2
0.6754	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6117	Approved
0.6667	Remote Similarity	NPD6052	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