NPASS Compound

Structure

CID227275 OpenBabel06191716022D 45 50 0 0 1 0 0 0 0 0999 V2000 5.4565 3.1503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4610 1.4104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3228 -0.1495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3392 -2.0225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7209 -1.2782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5829 -2.0543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2264 -2.1605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9383 -1.9497 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9296 2.4465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9372 -0.2969 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4520 1.4104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4474 1.9904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2409 -0.1838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7099 -0.5133 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3744 0.4701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4565 1.9904 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7918 -0.4790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7592 -1.0180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4429 1.4104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7582 -0.1730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8143 1.4104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8143 1.4104 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6286 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6286 1.8805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4429 0.4701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8143 0.4701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1597 1.8867 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8116 -1.1036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4638 0.3216 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8241 -0.9197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1963 -1.1726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1597 1.0640 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1567 -0.2227 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8143 0.4701 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6286 3.0405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0405 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3624 -1.3987 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2805 -1.4330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4150 0.5846 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3413 2.4463 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4913 0.3111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1416 -0.1590 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 -1.4958 -1.1726 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 5 31 1 0 0 0 0 6 31 1 0 0 0 0 7 32 1 0 0 0 0 8 32 1 0 0 0 0 9 41 1 0 0 0 0 10 42 1 0 0 0 0 11 12 1 0 0 0 0 11 16 2 0 0 0 0 12 19 1 0 0 0 0 13 14 1 0 0 0 0 13 17 2 0 0 0 0 14 34 1 0 0 0 0 15 20 1 0 0 0 0 15 33 1 0 0 0 0 17 29 1 0 0 0 0 18 4 1 6 0 0 0 18 31 1 0 0 0 0 18 43 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 32 1 0 0 0 0 20 35 1 1 0 0 0 21 24 1 0 0 0 0 21 25 1 0 0 0 0 21 27 2 0 0 0 0 22 25 1 0 0 0 0 22 28 1 0 0 0 0 22 35 1 6 0 0 0 23 26 2 0 0 0 0 23 27 1 0 0 0 0 23 31 1 0 0 0 0 24 36 1 0 0 0 0 25 37 2 0 0 0 0 26 43 1 0 0 0 0 27 44 1 0 0 0 0 28 33 1 1 0 0 0 28 41 1 0 0 0 0 29 38 2 0 0 0 0 29 39 1 0 0 0 0 30 33 1 0 0 0 0 30 34 1 0 0 0 0 30 40 2 0 0 0 0 32 45 1 0 0 0 0 33 42 1 6 0 0 0 34 35 1 1 0 0 0 34 45 1 0 0 0 0 35 44 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	624.29
Volume:	629.388
LogP:	6.26
LogD:	2.917
LogS:	-3.799
# Rotatable Bonds:	7
TPSA:	137.82
# H-Bond Aceptor:	10
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	7.303
Fsp3:	0.629
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:	-5.382
MDCK Permeability:	1.3730421414948069e-05
Pgp-inhibitor:	0.831
Pgp-substrate:	0.948
Human Intestinal Absorption (HIA):	0.508
20% Bioavailability (F20%):	0.104
30% Bioavailability (F30%):	0.746

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.432
Plasma Protein Binding (PPB):	90.03451538085938%
Volume Distribution (VD):	1.123
Pgp-substrate:	9.135891914367676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.057
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.267
CYP3A4-substrate:	0.784

ADMET: Excretion

Clearance (CL):	4.386
Half-life (T1/2):	0.06

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.943
Drug-inuced Liver Injury (DILI):	0.957
AMES Toxicity:	0.036
Rat Oral Acute Toxicity:	0.983
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.399
Carcinogencity:	0.821
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC227275

Natural Product ID:	NPC227275
*Common Name:**	Scortechinone I
IUPAC Name:	n.a.
Synonyms:	Scortechinone I
Standard InCHIKey:	WLNGEHPSYXBRGK-QBKFYMRTSA-N
Standard InCHI:	InChI=1S/C35H44O10/c1-16(2)11-12-19-24(36)21-25(37)22-28(41-9)33(42-10)15-20-32(7,8)45-34(30(33)40,14-13-17(3)29(38)39)35(20,22)44-27(21)23-26(19)43-18(4)31(23,5)6/h11,13,18,20,22,28,36H,12,14-15H2,1-10H3,(H,38,39)/b17-13-/t18-,20-,22+,28+,33+,34-,35-/m1/s1
SMILES:	CC(=CCc1c(c2C(=O)[C@H]3[C@@H]([C@]4(C[C@@H]5C(C)(C)O[C@](C/C=C(/C)C(=O)O)(C4=O)[C@]35Oc2c2c1O[C@H](C)C2(C)C)OC)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL500571
PubChem CID:	44559181
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	=	12800.0	nM	PMID[533151]

☑ 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 NPC227275 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	407
0.1-0.2	1595
0.2-0.3	3190
0.3-0.4	5968
0.4-0.5	10065
0.5-0.6	8206
0.6-0.7	5885
0.7-0.8	7002
0.8-0.85	302
0.85-0.9	44
0.9-0.95	25
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC475398
0.9641	High Similarity	NPC473607
0.9581	High Similarity	NPC233978
0.9524	High Similarity	NPC473729
0.9461	High Similarity	NPC162248
0.9401	High Similarity	NPC476152
0.9401	High Similarity	NPC476311
0.9349	High Similarity	NPC476210
0.9349	High Similarity	NPC476199
0.9341	High Similarity	NPC169018
0.929	High Similarity	NPC98943
0.9286	High Similarity	NPC476229
0.9286	High Similarity	NPC476139
0.9273	High Similarity	NPC473908
0.9222	High Similarity	NPC476146
0.9222	High Similarity	NPC158329
0.9222	High Similarity	NPC40089
0.9167	High Similarity	NPC476196
0.9157	High Similarity	NPC189689
0.9112	High Similarity	NPC476159
0.9107	High Similarity	NPC476216
0.9107	High Similarity	NPC75141
0.9107	High Similarity	NPC47634
0.9107	High Similarity	NPC41598
0.9107	High Similarity	NPC55422
0.9059	High Similarity	NPC475080
0.9	High Similarity	NPC118128
0.8935	High Similarity	NPC223413
0.8916	High Similarity	NPC286422
0.8882	High Similarity	NPC63514
0.8882	High Similarity	NPC102810
0.8876	High Similarity	NPC476255
0.8876	High Similarity	NPC62444
0.8869	High Similarity	NPC131578
0.8857	High Similarity	NPC475656
0.8857	High Similarity	NPC475148
0.8824	High Similarity	NPC193222
0.8765	High Similarity	NPC476056
0.8765	High Similarity	NPC475109
0.8728	High Similarity	NPC469393
0.8721	High Similarity	NPC193698
0.8698	High Similarity	NPC94796
0.8663	High Similarity	NPC54903
0.8663	High Similarity	NPC286074
0.8647	High Similarity	NPC476931
0.8644	High Similarity	NPC182693
0.8613	High Similarity	NPC315306
0.8613	High Similarity	NPC313717
0.8596	High Similarity	NPC316262
0.8596	High Similarity	NPC314653
0.8588	High Similarity	NPC475106
0.858	High Similarity	NPC43490
0.858	High Similarity	NPC475107
0.8571	High Similarity	NPC294149
0.8547	High Similarity	NPC17274
0.8547	High Similarity	NPC120857
0.8547	High Similarity	NPC469394
0.8547	High Similarity	NPC85047
0.8529	High Similarity	NPC476929
0.8514	High Similarity	NPC471969
0.8483	Intermediate Similarity	NPC208069
0.8462	Intermediate Similarity	NPC476930
0.8457	Intermediate Similarity	NPC472620
0.8457	Intermediate Similarity	NPC473113
0.8457	Intermediate Similarity	NPC477529
0.8448	Intermediate Similarity	NPC20734
0.8448	Intermediate Similarity	NPC473095
0.8448	Intermediate Similarity	NPC473096
0.8434	Intermediate Similarity	NPC476509
0.8434	Intermediate Similarity	NPC327059
0.8434	Intermediate Similarity	NPC321387
0.843	Intermediate Similarity	NPC469395
0.8421	Intermediate Similarity	NPC103816
0.8421	Intermediate Similarity	NPC61382
0.8418	Intermediate Similarity	NPC469345
0.8412	Intermediate Similarity	NPC125969
0.8402	Intermediate Similarity	NPC477674
0.84	Intermediate Similarity	NPC477670
0.8393	Intermediate Similarity	NPC477669
0.8391	Intermediate Similarity	NPC478059
0.8391	Intermediate Similarity	NPC473094
0.8391	Intermediate Similarity	NPC471975
0.8391	Intermediate Similarity	NPC478060
0.8391	Intermediate Similarity	NPC470374
0.8391	Intermediate Similarity	NPC470377
0.8383	Intermediate Similarity	NPC476162
0.8363	Intermediate Similarity	NPC313368
0.8363	Intermediate Similarity	NPC243701
0.8362	Intermediate Similarity	NPC86809
0.8362	Intermediate Similarity	NPC232412
0.8362	Intermediate Similarity	NPC98667
0.8343	Intermediate Similarity	NPC197972
0.8343	Intermediate Similarity	NPC477671
0.8343	Intermediate Similarity	NPC477687
0.8343	Intermediate Similarity	NPC291795
0.8343	Intermediate Similarity	NPC207574
0.8343	Intermediate Similarity	NPC297195
0.8343	Intermediate Similarity	NPC472619
0.8324	Intermediate Similarity	NPC208120
0.8324	Intermediate Similarity	NPC173587
0.8323	Intermediate Similarity	NPC470908
0.8315	Intermediate Similarity	NPC478050
0.8315	Intermediate Similarity	NPC312630
0.8315	Intermediate Similarity	NPC324220
0.8314	Intermediate Similarity	NPC117985
0.8314	Intermediate Similarity	NPC92589
0.8314	Intermediate Similarity	NPC472346
0.8306	Intermediate Similarity	NPC295436
0.8305	Intermediate Similarity	NPC470942
0.8297	Intermediate Similarity	NPC174486
0.8295	Intermediate Similarity	NPC251144
0.8295	Intermediate Similarity	NPC241387
0.8294	Intermediate Similarity	NPC474609
0.8294	Intermediate Similarity	NPC164427
0.8294	Intermediate Similarity	NPC109967
0.8294	Intermediate Similarity	NPC475797
0.8294	Intermediate Similarity	NPC321372
0.8294	Intermediate Similarity	NPC474738
0.8294	Intermediate Similarity	NPC470625
0.8294	Intermediate Similarity	NPC78554
0.8294	Intermediate Similarity	NPC129053
0.8294	Intermediate Similarity	NPC469936
0.8287	Intermediate Similarity	NPC106700
0.8286	Intermediate Similarity	NPC76647
0.8286	Intermediate Similarity	NPC232936
0.8286	Intermediate Similarity	NPC472622
0.8276	Intermediate Similarity	NPC146584
0.8276	Intermediate Similarity	NPC21016
0.8274	Intermediate Similarity	NPC477673
0.8274	Intermediate Similarity	NPC477672
0.827	Intermediate Similarity	NPC314020
0.8268	Intermediate Similarity	NPC477683
0.8268	Intermediate Similarity	NPC5671
0.8268	Intermediate Similarity	NPC477682
0.8266	Intermediate Similarity	NPC473022
0.8256	Intermediate Similarity	NPC472055
0.8246	Intermediate Similarity	NPC246466
0.8246	Intermediate Similarity	NPC196448
0.8239	Intermediate Similarity	NPC213416
0.8239	Intermediate Similarity	NPC288813
0.8239	Intermediate Similarity	NPC165456
0.8235	Intermediate Similarity	NPC478221
0.8235	Intermediate Similarity	NPC108937
0.8235	Intermediate Similarity	NPC279218
0.8235	Intermediate Similarity	NPC469934
0.8232	Intermediate Similarity	NPC472344
0.8232	Intermediate Similarity	NPC228209
0.8229	Intermediate Similarity	NPC13481
0.8229	Intermediate Similarity	NPC323137
0.8229	Intermediate Similarity	NPC207575
0.8229	Intermediate Similarity	NPC472621
0.8229	Intermediate Similarity	NPC20237
0.8229	Intermediate Similarity	NPC125465
0.8225	Intermediate Similarity	NPC470353
0.8218	Intermediate Similarity	NPC475055
0.8218	Intermediate Similarity	NPC29055
0.8218	Intermediate Similarity	NPC249181
0.8214	Intermediate Similarity	NPC180351
0.8208	Intermediate Similarity	NPC187354
0.8207	Intermediate Similarity	NPC314672
0.8204	Intermediate Similarity	NPC472345
0.8202	Intermediate Similarity	NPC474276
0.8202	Intermediate Similarity	NPC73899
0.8202	Intermediate Similarity	NPC17105
0.8202	Intermediate Similarity	NPC147363
0.8198	Intermediate Similarity	NPC239118
0.8198	Intermediate Similarity	NPC470339
0.8197	Intermediate Similarity	NPC294863
0.8197	Intermediate Similarity	NPC240808
0.8197	Intermediate Similarity	NPC282636
0.8193	Intermediate Similarity	NPC470910
0.8192	Intermediate Similarity	NPC472276
0.8187	Intermediate Similarity	NPC470352
0.8187	Intermediate Similarity	NPC470354
0.8187	Intermediate Similarity	NPC474386
0.8187	Intermediate Similarity	NPC477675
0.8182	Intermediate Similarity	NPC45760
0.8182	Intermediate Similarity	NPC307895
0.8182	Intermediate Similarity	NPC158761
0.8182	Intermediate Similarity	NPC283041
0.8182	Intermediate Similarity	NPC126204
0.8182	Intermediate Similarity	NPC470456
0.8182	Intermediate Similarity	NPC470553
0.8176	Intermediate Similarity	NPC478231
0.8176	Intermediate Similarity	NPC236756
0.8176	Intermediate Similarity	NPC471695
0.8176	Intermediate Similarity	NPC311579
0.8176	Intermediate Similarity	NPC75310
0.8171	Intermediate Similarity	NPC191930
0.8171	Intermediate Similarity	NPC270312
0.8171	Intermediate Similarity	NPC473766
0.8171	Intermediate Similarity	NPC294722
0.8171	Intermediate Similarity	NPC473753
0.8171	Intermediate Similarity	NPC472049
0.8167	Intermediate Similarity	NPC23553
0.8167	Intermediate Similarity	NPC77179
0.8166	Intermediate Similarity	NPC473131
0.8166	Intermediate Similarity	NPC470675
0.8166	Intermediate Similarity	NPC290671
0.8161	Intermediate Similarity	NPC472402

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 NPC227275 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	964
0.2-0.3	2032
0.3-0.4	2641
0.4-0.5	1909
0.5-0.6	877
0.6-0.7	237
0.7-0.8	133
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
0.8246	Intermediate Similarity	NPD7075	Discontinued
0.8177	Intermediate Similarity	NPD8434	Phase 2
0.807	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD2532	Approved
0.8024	Intermediate Similarity	NPD2534	Approved
0.8024	Intermediate Similarity	NPD2533	Approved
0.8023	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6801	Discontinued
0.7965	Intermediate Similarity	NPD7819	Suspended
0.7939	Intermediate Similarity	NPD2800	Approved
0.7933	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD6599	Discontinued
0.7886	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7411	Suspended
0.7841	Intermediate Similarity	NPD5494	Approved
0.7821	Intermediate Similarity	NPD7473	Discontinued
0.7816	Intermediate Similarity	NPD5402	Approved
0.7816	Intermediate Similarity	NPD3817	Phase 2
0.7811	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4380	Phase 2
0.7771	Intermediate Similarity	NPD3882	Suspended
0.7765	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD3818	Discontinued
0.767	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7663	Intermediate Similarity	NPD7808	Phase 3
0.7657	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6232	Discontinued
0.7647	Intermediate Similarity	NPD6799	Approved
0.7637	Intermediate Similarity	NPD5844	Phase 1
0.7627	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD5403	Approved
0.7609	Intermediate Similarity	NPD7251	Discontinued
0.7598	Intermediate Similarity	NPD1247	Approved
0.7598	Intermediate Similarity	NPD6959	Discontinued
0.7594	Intermediate Similarity	NPD8150	Discontinued
0.7576	Intermediate Similarity	NPD6651	Approved
0.7571	Intermediate Similarity	NPD7768	Phase 2
0.7569	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD6166	Phase 2
0.7557	Intermediate Similarity	NPD2801	Approved
0.7554	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD6797	Phase 2
0.7528	Intermediate Similarity	NPD3749	Approved
0.7514	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD5401	Approved
0.75	Intermediate Similarity	NPD1934	Approved
0.7486	Intermediate Similarity	NPD919	Approved
0.7471	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD3750	Approved
0.7459	Intermediate Similarity	NPD5710	Approved
0.7459	Intermediate Similarity	NPD5711	Approved
0.7456	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7446	Intermediate Similarity	NPD7054	Approved
0.7429	Intermediate Similarity	NPD3226	Approved
0.7421	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7472	Approved
0.7405	Intermediate Similarity	NPD7074	Phase 3
0.7371	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD1512	Approved
0.7353	Intermediate Similarity	NPD1549	Phase 2
0.734	Intermediate Similarity	NPD8313	Approved
0.734	Intermediate Similarity	NPD8312	Approved
0.7337	Intermediate Similarity	NPD2796	Approved
0.7323	Intermediate Similarity	NPD7435	Discontinued
0.7314	Intermediate Similarity	NPD920	Approved
0.731	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD3751	Discontinued
0.7294	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD6234	Discontinued
0.7283	Intermediate Similarity	NPD2403	Approved
0.7278	Intermediate Similarity	NPD4967	Phase 2
0.7278	Intermediate Similarity	NPD4965	Approved
0.7278	Intermediate Similarity	NPD1510	Phase 2
0.7278	Intermediate Similarity	NPD4966	Approved
0.7267	Intermediate Similarity	NPD4628	Phase 3
0.7263	Intermediate Similarity	NPD1465	Phase 2
0.7241	Intermediate Similarity	NPD1511	Approved
0.7235	Intermediate Similarity	NPD6099	Approved
0.7235	Intermediate Similarity	NPD6100	Approved
0.7234	Intermediate Similarity	NPD6764	Approved
0.7234	Intermediate Similarity	NPD6765	Approved
0.7228	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD1243	Approved
0.7207	Intermediate Similarity	NPD37	Approved
0.7204	Intermediate Similarity	NPD7228	Approved
0.7204	Intermediate Similarity	NPD7799	Discontinued
0.72	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD7874	Approved
0.7192	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3748	Approved
0.7167	Intermediate Similarity	NPD5761	Phase 2
0.7167	Intermediate Similarity	NPD5760	Phase 2
0.715	Intermediate Similarity	NPD7697	Approved
0.715	Intermediate Similarity	NPD7696	Phase 3
0.715	Intermediate Similarity	NPD7698	Approved
0.7143	Intermediate Similarity	NPD8151	Discontinued
0.7135	Intermediate Similarity	NPD7458	Discontinued
0.7135	Intermediate Similarity	NPD2935	Discontinued
0.7135	Intermediate Similarity	NPD3926	Phase 2
0.712	Intermediate Similarity	NPD8407	Phase 2
0.712	Intermediate Similarity	NPD8127	Discontinued
0.7114	Intermediate Similarity	NPD7871	Phase 2
0.7114	Intermediate Similarity	NPD7870	Phase 2
0.7101	Intermediate Similarity	NPD5124	Phase 1
0.7101	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD8366	Approved
0.7095	Intermediate Similarity	NPD7907	Approved
0.7093	Intermediate Similarity	NPD2346	Discontinued
0.709	Intermediate Similarity	NPD5953	Discontinued
0.7089	Intermediate Similarity	NPD8469	Approved
0.7086	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6780	Approved
0.7085	Intermediate Similarity	NPD6776	Approved
0.7085	Intermediate Similarity	NPD6781	Approved
0.7085	Intermediate Similarity	NPD6777	Approved
0.7085	Intermediate Similarity	NPD6778	Approved
0.7085	Intermediate Similarity	NPD6779	Approved
0.7085	Intermediate Similarity	NPD6782	Approved
0.7083	Intermediate Similarity	NPD6784	Approved
0.7083	Intermediate Similarity	NPD6785	Approved
0.7081	Intermediate Similarity	NPD3787	Discontinued
0.7076	Intermediate Similarity	NPD2799	Discontinued
0.7074	Intermediate Similarity	NPD7286	Phase 2
0.7067	Intermediate Similarity	NPD8404	Phase 2
0.7059	Intermediate Similarity	NPD1607	Approved
0.7053	Intermediate Similarity	NPD8368	Discontinued
0.7042	Intermediate Similarity	NPD8491	Approved
0.7041	Intermediate Similarity	NPD1240	Approved
0.7035	Intermediate Similarity	NPD1551	Phase 2
0.7035	Intermediate Similarity	NPD8285	Discontinued
0.703	Intermediate Similarity	NPD8319	Approved
0.703	Intermediate Similarity	NPD8320	Phase 1
0.7027	Intermediate Similarity	NPD7199	Phase 2
0.7024	Intermediate Similarity	NPD2313	Discontinued
0.7021	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7701	Phase 2
0.7006	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7783	Phase 2
0.699	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7801	Approved
0.6989	Remote Similarity	NPD7229	Phase 3
0.6989	Remote Similarity	NPD7236	Approved
0.6985	Remote Similarity	NPD7699	Phase 2
0.6985	Remote Similarity	NPD7700	Phase 2
0.6971	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7685	Pre-registration
0.6932	Remote Similarity	NPD6190	Approved
0.6927	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6534	Approved
0.6919	Remote Similarity	NPD6535	Approved
0.6901	Remote Similarity	NPD6355	Discontinued
0.6897	Remote Similarity	NPD1471	Phase 3
0.6889	Remote Similarity	NPD7239	Suspended
0.6888	Remote Similarity	NPD8435	Approved
0.6888	Remote Similarity	NPD8361	Approved
0.6888	Remote Similarity	NPD8360	Approved
0.6879	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7240	Approved
0.6872	Remote Similarity	NPD6273	Approved
0.6854	Remote Similarity	NPD7390	Discontinued
0.6854	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.684	Remote Similarity	NPD4111	Phase 1
0.684	Remote Similarity	NPD4665	Approved
0.6824	Remote Similarity	NPD3268	Approved
0.6802	Remote Similarity	NPD4287	Approved
0.6802	Remote Similarity	NPD230	Phase 1
0.68	Remote Similarity	NPD2344	Approved
0.68	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD7584	Approved
0.6791	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD7033	Discontinued
0.678	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.678	Remote Similarity	NPD7003	Approved
0.678	Remote Similarity	NPD8166	Discontinued
0.6776	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD8485	Approved
0.6765	Remote Similarity	NPD6823	Phase 2
0.676	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD8067	Phase 3
0.675	Remote Similarity	NPD4360	Phase 2
0.675	Remote Similarity	NPD4363	Phase 3
0.6744	Remote Similarity	NPD4060	Phase 1
0.6732	Remote Similarity	NPD7497	Discontinued
0.6725	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD6832	Phase 2
0.6705	Remote Similarity	NPD6004	Phase 3
0.6705	Remote Similarity	NPD6002	Phase 3
0.6705	Remote Similarity	NPD6006	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