NPASS Compound

Structure

CID169018 OpenBabel06191715542D 41 46 0 0 1 0 0 0 0 0999 V2000 4.0065 -0.8185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8145 -0.8185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4411 -0.9723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9960 -1.8387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0050 -1.8201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6488 -1.1503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4245 -1.8487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2037 -1.9443 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -1.7546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7422 -0.1539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9105 0.7473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1024 1.7912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4682 -1.0200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4406 -0.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0437 1.6979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3369 0.4231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9105 -0.2965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9684 -1.2770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4831 -0.9161 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1984 1.2693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7328 1.2693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6823 -0.1557 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7328 1.2693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4656 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4656 1.6924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1984 0.4231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7328 0.4231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2172 0.2894 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6416 -0.8277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1766 -1.0553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0437 0.9575 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9409 -0.2004 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7328 0.4231 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4656 2.7362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.7362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1039 0.5346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3421 0.2800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8273 -0.1431 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 -1.3461 -1.0553 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 6 30 1 0 0 0 0 7 30 1 0 0 0 0 8 31 1 0 0 0 0 9 31 1 0 0 0 0 10 38 1 0 0 0 0 11 12 1 0 0 0 0 11 17 2 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 18 2 0 0 0 0 14 33 1 0 0 0 0 15 21 2 0 0 0 0 15 32 1 0 0 0 0 16 22 1 0 0 0 0 16 32 1 0 0 0 0 19 5 1 6 0 0 0 19 30 1 0 0 0 0 19 39 1 0 0 0 0 20 25 2 0 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 22 31 1 0 0 0 0 22 34 1 1 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 23 28 2 0 0 0 0 24 27 2 0 0 0 0 24 28 1 0 0 0 0 24 30 1 0 0 0 0 25 35 1 0 0 0 0 26 36 2 0 0 0 0 27 39 1 0 0 0 0 28 40 1 0 0 0 0 29 32 1 0 0 0 0 29 33 1 0 0 0 0 29 37 2 0 0 0 0 31 41 1 0 0 0 0 32 38 1 6 0 0 0 33 34 1 1 0 0 0 33 41 1 0 0 0 0 34 21 1 1 0 0 0 34 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.29
Volume:	585.721
LogP:	7.775
LogD:	4.256
LogS:	-4.71
# Rotatable Bonds:	5
TPSA:	91.29
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	6.754
Fsp3:	0.588
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.751
MDCK Permeability:	1.6792037058621645e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.925
Human Intestinal Absorption (HIA):	0.326
20% Bioavailability (F20%):	0.348
30% Bioavailability (F30%):	0.591

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.214
Plasma Protein Binding (PPB):	88.78239440917969%
Volume Distribution (VD):	2.005
Pgp-substrate:	8.933191299438477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.077
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.506
CYP2C19-substrate:	0.879
CYP2C9-inhibitor:	0.717
CYP2C9-substrate:	0.162
CYP2D6-inhibitor:	0.337
CYP2D6-substrate:	0.065
CYP3A4-inhibitor:	0.827
CYP3A4-substrate:	0.933

ADMET: Excretion

Clearance (CL):	11.289
Half-life (T1/2):	0.033

ADMET: Toxicity

hERG Blockers:	0.515
Human Hepatotoxicity (H-HT):	0.984
Drug-inuced Liver Injury (DILI):	0.557
AMES Toxicity:	0.083
Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.596
Carcinogencity:	0.949
Eye Corrosion:	0.003
Eye Irritation:	0.038
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC169018

Natural Product ID:	NPC169018
*Common Name:**	Scortechinone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JXVGZQWFGMBBFV-UORHYOFISA-N
Standard InCHI:	InChI=1S/C34H42O7/c1-17(2)11-12-20-25(35)23-26(36)21-15-32(38-10)16-22-31(8,9)41-33(29(32)37,14-13-18(3)4)34(21,22)40-28(23)24-27(20)39-19(5)30(24,6)7/h11,13,15,19,22,35H,12,14,16H2,1-10H3/t19-,22-,32-,33-,34+/m1/s1
SMILES:	CO[C@]12C=C3C(=O)c4c(O)c(CC=C(C)C)c5c(c4O[C@@]43[C@H](C1)C(O[C@@]4(C2=O)CC=C(C)C)(C)C)C(C)(C)[C@H](O5)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449482
PubChem CID:	44559179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16038540]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	228000.0	nM	PMID[461170]

☑ 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 NPC169018 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	432
0.1-0.2	1565
0.2-0.3	3125
0.3-0.4	6495
0.4-0.5	10869
0.5-0.6	6837
0.6-0.7	5861
0.7-0.8	7009
0.8-0.85	418
0.85-0.9	24
0.9-0.95	48
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
0.9816	High Similarity	NPC98943
0.9756	High Similarity	NPC233978
0.9693	High Similarity	NPC475080
0.9578	High Similarity	NPC473607
0.9461	High Similarity	NPC473729
0.9437	High Similarity	NPC286422
0.9398	High Similarity	NPC475398
0.9398	High Similarity	NPC162248
0.9394	High Similarity	NPC476159
0.9387	High Similarity	NPC62444
0.9387	High Similarity	NPC476255
0.9387	High Similarity	NPC475109
0.9341	High Similarity	NPC227275
0.9329	High Similarity	NPC193222
0.9329	High Similarity	NPC223413
0.9277	High Similarity	NPC118128
0.9268	High Similarity	NPC476056
0.9264	High Similarity	NPC131578
0.9222	High Similarity	NPC476139
0.9222	High Similarity	NPC476229
0.9222	High Similarity	NPC476311
0.9207	High Similarity	NPC189689
0.9202	High Similarity	NPC94796
0.9146	High Similarity	NPC476931
0.9107	High Similarity	NPC476152
0.908	High Similarity	NPC43490
0.908	High Similarity	NPC475107
0.9059	High Similarity	NPC476210
0.9059	High Similarity	NPC476199
0.9042	High Similarity	NPC476216
0.9042	High Similarity	NPC63514
0.9042	High Similarity	NPC75141
0.9042	High Similarity	NPC55422
0.9042	High Similarity	NPC47634
0.8929	High Similarity	NPC40089
0.8929	High Similarity	NPC476146
0.8929	High Similarity	NPC41598
0.8929	High Similarity	NPC158329
0.8882	High Similarity	NPC476162
0.8876	High Similarity	NPC476196
0.8862	High Similarity	NPC473908
0.8855	High Similarity	NPC475106
0.8795	High Similarity	NPC476929
0.8793	High Similarity	NPC475148
0.8793	High Similarity	NPC475656
0.8772	High Similarity	NPC469393
0.8765	High Similarity	NPC313717
0.8765	High Similarity	NPC315306
0.875	High Similarity	NPC314653
0.875	High Similarity	NPC316262
0.8706	High Similarity	NPC286074
0.8706	High Similarity	NPC54903
0.8623	High Similarity	NPC313368
0.8605	High Similarity	NPC477529
0.8596	High Similarity	NPC102810
0.8588	High Similarity	NPC17274
0.8588	High Similarity	NPC85047
0.8588	High Similarity	NPC469394
0.8588	High Similarity	NPC120857
0.858	High Similarity	NPC469395
0.858	High Similarity	NPC475055
0.8563	High Similarity	NPC125969
0.8555	High Similarity	NPC471969
0.8554	High Similarity	NPC164427
0.8514	High Similarity	NPC5671
0.8503	High Similarity	NPC476930
0.8503	High Similarity	NPC196448
0.8488	Intermediate Similarity	NPC20734
0.8476	Intermediate Similarity	NPC476509
0.8475	Intermediate Similarity	NPC8927
0.8471	Intermediate Similarity	NPC208120
0.8471	Intermediate Similarity	NPC109180
0.8471	Intermediate Similarity	NPC173587
0.8462	Intermediate Similarity	NPC103816
0.8462	Intermediate Similarity	NPC61382
0.8457	Intermediate Similarity	NPC478050
0.8439	Intermediate Similarity	NPC193698
0.843	Intermediate Similarity	NPC232936
0.843	Intermediate Similarity	NPC470377
0.843	Intermediate Similarity	NPC476459
0.843	Intermediate Similarity	NPC470374
0.843	Intermediate Similarity	NPC471975
0.843	Intermediate Similarity	NPC478059
0.843	Intermediate Similarity	NPC478060
0.8424	Intermediate Similarity	NPC473131
0.8424	Intermediate Similarity	NPC470675
0.8421	Intermediate Similarity	NPC146584
0.8421	Intermediate Similarity	NPC21016
0.8409	Intermediate Similarity	NPC221820
0.84	Intermediate Similarity	NPC294149
0.8391	Intermediate Similarity	NPC472620
0.8385	Intermediate Similarity	NPC276565
0.8383	Intermediate Similarity	NPC471116
0.8382	Intermediate Similarity	NPC288813
0.8382	Intermediate Similarity	NPC213416
0.8382	Intermediate Similarity	NPC152477
0.8373	Intermediate Similarity	NPC288534
0.8373	Intermediate Similarity	NPC470353
0.8372	Intermediate Similarity	NPC82330
0.8371	Intermediate Similarity	NPC182693
0.8371	Intermediate Similarity	NPC228209
0.8363	Intermediate Similarity	NPC472582
0.8363	Intermediate Similarity	NPC18100
0.8363	Intermediate Similarity	NPC473313
0.8363	Intermediate Similarity	NPC472278
0.8363	Intermediate Similarity	NPC472581
0.8363	Intermediate Similarity	NPC273959
0.8363	Intermediate Similarity	NPC329669
0.8362	Intermediate Similarity	NPC476273
0.8352	Intermediate Similarity	NPC469345
0.8344	Intermediate Similarity	NPC82534
0.8343	Intermediate Similarity	NPC470942
0.8333	Intermediate Similarity	NPC470352
0.8333	Intermediate Similarity	NPC18886
0.8333	Intermediate Similarity	NPC472276
0.8333	Intermediate Similarity	NPC477670
0.8333	Intermediate Similarity	NPC240808
0.8333	Intermediate Similarity	NPC477674
0.8324	Intermediate Similarity	NPC150131
0.8324	Intermediate Similarity	NPC45760
0.8323	Intermediate Similarity	NPC100134
0.8323	Intermediate Similarity	NPC111201
0.8323	Intermediate Similarity	NPC209760
0.8323	Intermediate Similarity	NPC311579
0.8323	Intermediate Similarity	NPC236756
0.8323	Intermediate Similarity	NPC477669
0.8323	Intermediate Similarity	NPC74397
0.8315	Intermediate Similarity	NPC208069
0.8314	Intermediate Similarity	NPC473286
0.8314	Intermediate Similarity	NPC300053
0.8314	Intermediate Similarity	NPC472277
0.8305	Intermediate Similarity	NPC23553
0.8305	Intermediate Similarity	NPC77179
0.8305	Intermediate Similarity	NPC246877
0.8304	Intermediate Similarity	NPC472402
0.8295	Intermediate Similarity	NPC289244
0.8295	Intermediate Similarity	NPC245975
0.8295	Intermediate Similarity	NPC98667
0.8295	Intermediate Similarity	NPC86809
0.8295	Intermediate Similarity	NPC232412
0.8294	Intermediate Similarity	NPC472618
0.8294	Intermediate Similarity	NPC470810
0.8286	Intermediate Similarity	NPC121333
0.8284	Intermediate Similarity	NPC201127
0.8278	Intermediate Similarity	NPC197972
0.8276	Intermediate Similarity	NPC297195
0.8276	Intermediate Similarity	NPC472619
0.8276	Intermediate Similarity	NPC291795
0.8276	Intermediate Similarity	NPC207574
0.8276	Intermediate Similarity	NPC242395
0.8276	Intermediate Similarity	NPC165456
0.8274	Intermediate Similarity	NPC476169
0.8274	Intermediate Similarity	NPC175192
0.8274	Intermediate Similarity	NPC326910
0.8268	Intermediate Similarity	NPC246153
0.8266	Intermediate Similarity	NPC53640
0.8266	Intermediate Similarity	NPC128293
0.8266	Intermediate Similarity	NPC173292
0.8266	Intermediate Similarity	NPC119589
0.8266	Intermediate Similarity	NPC170245
0.8263	Intermediate Similarity	NPC473996
0.8263	Intermediate Similarity	NPC477957
0.8263	Intermediate Similarity	NPC275878
0.8263	Intermediate Similarity	NPC210597
0.8261	Intermediate Similarity	NPC164697
0.8261	Intermediate Similarity	NPC82920
0.8261	Intermediate Similarity	NPC289660
0.8256	Intermediate Similarity	NPC474240
0.8256	Intermediate Similarity	NPC205265
0.8256	Intermediate Similarity	NPC472281
0.8256	Intermediate Similarity	NPC476822
0.8256	Intermediate Similarity	NPC100849
0.8249	Intermediate Similarity	NPC312630
0.8249	Intermediate Similarity	NPC324220
0.8246	Intermediate Similarity	NPC3629
0.8246	Intermediate Similarity	NPC187354
0.8246	Intermediate Similarity	NPC474186
0.8246	Intermediate Similarity	NPC478134
0.8246	Intermediate Similarity	NPC472346
0.8246	Intermediate Similarity	NPC117985
0.8246	Intermediate Similarity	NPC475883
0.8246	Intermediate Similarity	NPC474351
0.8239	Intermediate Similarity	NPC474276
0.8239	Intermediate Similarity	NPC73899
0.8239	Intermediate Similarity	NPC154986
0.8239	Intermediate Similarity	NPC17105
0.8239	Intermediate Similarity	NPC147363
0.8235	Intermediate Similarity	NPC40583
0.8235	Intermediate Similarity	NPC472617
0.8229	Intermediate Similarity	NPC251144
0.8229	Intermediate Similarity	NPC241387
0.8225	Intermediate Similarity	NPC20530
0.8225	Intermediate Similarity	NPC10754
0.8225	Intermediate Similarity	NPC215917
0.8225	Intermediate Similarity	NPC474386
0.8225	Intermediate Similarity	NPC470354
0.8222	Intermediate Similarity	NPC476170
0.8221	Intermediate Similarity	NPC5990
0.8218	Intermediate Similarity	NPC472622
0.8218	Intermediate Similarity	NPC225419

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 NPC169018 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	928
0.2-0.3	1989
0.3-0.4	2681
0.4-0.5	1910
0.5-0.6	872
0.6-0.7	276
0.7-0.8	124
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8199	Intermediate Similarity	NPD2800	Approved
0.8166	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD5494	Approved
0.807	Intermediate Similarity	NPD7075	Discontinued
0.8	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD2532	Approved
0.7952	Intermediate Similarity	NPD2533	Approved
0.7952	Intermediate Similarity	NPD2534	Approved
0.7919	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7912	Intermediate Similarity	NPD8434	Phase 2
0.7907	Intermediate Similarity	NPD3882	Suspended
0.7895	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7844	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD4380	Phase 2
0.7791	Intermediate Similarity	NPD7819	Suspended
0.7733	Intermediate Similarity	NPD1934	Approved
0.7727	Intermediate Similarity	NPD6959	Discontinued
0.7727	Intermediate Similarity	NPD1247	Approved
0.7719	Intermediate Similarity	NPD6599	Discontinued
0.7716	Intermediate Similarity	NPD6651	Approved
0.7697	Intermediate Similarity	NPD6166	Phase 2
0.7697	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7411	Suspended
0.7647	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6801	Discontinued
0.7598	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7596	Intermediate Similarity	NPD7808	Phase 3
0.759	Intermediate Similarity	NPD1549	Phase 2
0.7586	Intermediate Similarity	NPD2801	Approved
0.7569	Intermediate Similarity	NPD5844	Phase 1
0.7568	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD7473	Discontinued
0.7541	Intermediate Similarity	NPD7251	Discontinued
0.753	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD8150	Discontinued
0.7514	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2403	Approved
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5711	Approved
0.7486	Intermediate Similarity	NPD6797	Phase 2
0.7486	Intermediate Similarity	NPD5710	Approved
0.7471	Intermediate Similarity	NPD6799	Approved
0.747	Intermediate Similarity	NPD6100	Approved
0.747	Intermediate Similarity	NPD6099	Approved
0.7458	Intermediate Similarity	NPD3749	Approved
0.7446	Intermediate Similarity	NPD6559	Discontinued
0.7443	Intermediate Similarity	NPD5402	Approved
0.7443	Intermediate Similarity	NPD3817	Phase 2
0.7432	Intermediate Similarity	NPD7074	Phase 3
0.7418	Intermediate Similarity	NPD3751	Discontinued
0.7401	Intermediate Similarity	NPD7768	Phase 2
0.7391	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6232	Discontinued
0.7384	Intermediate Similarity	NPD1512	Approved
0.7377	Intermediate Similarity	NPD7054	Approved
0.7365	Intermediate Similarity	NPD2796	Approved
0.7337	Intermediate Similarity	NPD7472	Approved
0.7318	Intermediate Similarity	NPD919	Approved
0.7305	Intermediate Similarity	NPD1510	Phase 2
0.7288	Intermediate Similarity	NPD5760	Phase 2
0.7288	Intermediate Similarity	NPD5761	Phase 2
0.7282	Intermediate Similarity	NPD7907	Approved
0.7278	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1511	Approved
0.7263	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5403	Approved
0.7198	Intermediate Similarity	NPD3787	Discontinued
0.7193	Intermediate Similarity	NPD3750	Approved
0.7186	Intermediate Similarity	NPD1607	Approved
0.7181	Intermediate Similarity	NPD8313	Approved
0.7181	Intermediate Similarity	NPD8312	Approved
0.7172	Intermediate Similarity	NPD7435	Discontinued
0.7172	Intermediate Similarity	NPD7697	Approved
0.7172	Intermediate Similarity	NPD7696	Phase 3
0.7172	Intermediate Similarity	NPD7698	Approved
0.7169	Intermediate Similarity	NPD1240	Approved
0.7159	Intermediate Similarity	NPD3226	Approved
0.7158	Intermediate Similarity	NPD3926	Phase 2
0.7143	Intermediate Similarity	NPD920	Approved
0.7136	Intermediate Similarity	NPD7871	Phase 2
0.7136	Intermediate Similarity	NPD7870	Phase 2
0.7135	Intermediate Similarity	NPD7228	Approved
0.7135	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD6234	Discontinued
0.7126	Intermediate Similarity	NPD5401	Approved
0.7111	Intermediate Similarity	NPD4965	Approved
0.7111	Intermediate Similarity	NPD4967	Phase 2
0.7111	Intermediate Similarity	NPD4966	Approved
0.7107	Intermediate Similarity	NPD6782	Approved
0.7107	Intermediate Similarity	NPD6780	Approved
0.7107	Intermediate Similarity	NPD6776	Approved
0.7107	Intermediate Similarity	NPD6777	Approved
0.7107	Intermediate Similarity	NPD6779	Approved
0.7107	Intermediate Similarity	NPD6778	Approved
0.7107	Intermediate Similarity	NPD6781	Approved
0.7107	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4111	Phase 1
0.7101	Intermediate Similarity	NPD4665	Approved
0.7095	Intermediate Similarity	NPD1465	Phase 2
0.7093	Intermediate Similarity	NPD4628	Phase 3
0.7074	Intermediate Similarity	NPD6765	Approved
0.7074	Intermediate Similarity	NPD6764	Approved
0.7048	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7874	Approved
0.7044	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD1243	Approved
0.7033	Intermediate Similarity	NPD8366	Approved
0.703	Intermediate Similarity	NPD7701	Phase 2
0.7029	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5124	Phase 1
0.7024	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2346	Discontinued
0.7018	Intermediate Similarity	NPD1471	Phase 3
0.701	Intermediate Similarity	NPD7801	Approved
0.7005	Intermediate Similarity	NPD7699	Phase 2
0.7005	Intermediate Similarity	NPD7700	Phase 2
0.7	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8151	Discontinued
0.6981	Remote Similarity	NPD8491	Approved
0.6973	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7458	Discontinued
0.6959	Remote Similarity	NPD2935	Discontinued
0.6952	Remote Similarity	NPD7799	Discontinued
0.6948	Remote Similarity	NPD8469	Approved
0.6944	Remote Similarity	NPD37	Approved
0.6939	Remote Similarity	NPD6535	Approved
0.6939	Remote Similarity	NPD6534	Approved
0.6932	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD6785	Approved
0.6927	Remote Similarity	NPD6784	Approved
0.6919	Remote Similarity	NPD2344	Approved
0.6915	Remote Similarity	NPD7286	Phase 2
0.6914	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3748	Approved
0.6901	Remote Similarity	NPD2799	Discontinued
0.6881	Remote Similarity	NPD8320	Phase 1
0.6881	Remote Similarity	NPD8319	Approved
0.6875	Remote Similarity	NPD8407	Phase 2
0.6875	Remote Similarity	NPD7390	Discontinued
0.6866	Remote Similarity	NPD3057	Approved
0.6865	Remote Similarity	NPD8127	Discontinued
0.6862	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1551	Phase 2
0.6853	Remote Similarity	NPD4360	Phase 2
0.6853	Remote Similarity	NPD4363	Phase 3
0.6845	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7783	Phase 2
0.6842	Remote Similarity	NPD5953	Discontinued
0.6842	Remote Similarity	NPD8404	Phase 2
0.6828	Remote Similarity	NPD7229	Phase 3
0.6818	Remote Similarity	NPD7236	Approved
0.6816	Remote Similarity	NPD2493	Approved
0.6816	Remote Similarity	NPD2494	Approved
0.6806	Remote Similarity	NPD7240	Approved
0.6806	Remote Similarity	NPD8368	Discontinued
0.6802	Remote Similarity	NPD651	Clinical (unspecified phase)
0.68	Remote Similarity	NPD8285	Discontinued
0.68	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD4583	Approved
0.6798	Remote Similarity	NPD4582	Approved
0.6784	Remote Similarity	NPD2973	Approved
0.6784	Remote Similarity	NPD2975	Approved
0.6784	Remote Similarity	NPD2974	Approved
0.6782	Remote Similarity	NPD2972	Approved
0.6782	Remote Similarity	NPD3533	Approved
0.6782	Remote Similarity	NPD6823	Phase 2
0.6778	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7199	Phase 2
0.6773	Remote Similarity	NPD7048	Phase 3
0.6766	Remote Similarity	NPD4580	Approved
0.6761	Remote Similarity	NPD2309	Approved
0.6749	Remote Similarity	NPD4002	Approved
0.6749	Remote Similarity	NPD4004	Approved
0.6746	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD2313	Discontinued
0.6735	Remote Similarity	NPD4287	Approved
0.6733	Remote Similarity	NPD3452	Approved
0.6733	Remote Similarity	NPD3450	Approved
0.6732	Remote Similarity	NPD7584	Approved
0.6729	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4749	Approved
0.6726	Remote Similarity	NPD4908	Phase 1
0.6725	Remote Similarity	NPD6355	Discontinued
0.6725	Remote Similarity	NPD230	Phase 1
0.6723	Remote Similarity	NPD3300	Phase 2
0.6719	Remote Similarity	NPD7685	Pre-registration
0.6714	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6704	Remote Similarity	NPD6273	Approved
0.6703	Remote Similarity	NPD7615	Clinical (unspecified phase)

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