NPASS Compound

Structure

CID233978 OpenBabel06191716032D 43 48 0 0 1 0 0 0 0 0999 V2000 5.4271 3.1334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4263 1.4028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3203 -0.7722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3212 -2.0117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7170 -1.2713 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5744 -2.0433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2252 -2.1489 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9333 -1.9392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8730 -0.2356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4280 1.4028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4289 1.9797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3099 -0.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6974 -0.5065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1535 1.8765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3724 0.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4271 1.9797 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7078 -0.8781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7444 -1.0125 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4297 1.4028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8099 1.4028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7541 -0.1721 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8099 1.4028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6198 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6198 1.8704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4297 0.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8099 0.4676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4933 -1.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4505 0.3199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8143 -0.9148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1952 -1.1663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1535 1.0583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1451 -0.2215 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8099 0.4676 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6198 3.0241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8912 -1.9389 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8808 -1.5673 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4136 0.5861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4833 0.3095 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1247 -0.1582 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 -1.4878 -1.1663 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 30 1 0 0 0 0 6 30 1 0 0 0 0 7 31 1 0 0 0 0 8 31 1 0 0 0 0 9 40 1 0 0 0 0 10 11 1 0 0 0 0 10 16 2 0 0 0 0 11 19 1 0 0 0 0 12 13 1 0 0 0 0 12 17 2 0 0 0 0 13 33 1 0 0 0 0 14 20 2 0 0 0 0 14 32 1 0 0 0 0 15 21 1 0 0 0 0 15 32 1 0 0 0 0 17 28 1 0 0 0 0 18 4 1 1 0 0 0 18 30 1 0 0 0 0 18 41 1 0 0 0 0 19 24 2 0 0 0 0 19 26 1 0 0 0 0 20 25 1 0 0 0 0 21 31 1 0 0 0 0 21 34 1 1 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 22 27 2 0 0 0 0 23 26 2 0 0 0 0 23 27 1 0 0 0 0 23 30 1 0 0 0 0 24 35 1 0 0 0 0 25 36 2 0 0 0 0 26 41 1 0 0 0 0 27 42 1 0 0 0 0 28 37 2 0 0 0 0 28 38 1 0 0 0 0 29 32 1 0 0 0 0 29 33 1 0 0 0 0 29 39 2 0 0 0 0 31 43 1 0 0 0 0 32 40 1 6 0 0 0 33 34 1 1 0 0 0 33 43 1 0 0 0 0 34 20 1 1 0 0 0 34 42 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	592.27
Volume:	600.665
LogP:	6.389
LogD:	2.683
LogS:	-3.656
# Rotatable Bonds:	6
TPSA:	128.59
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.438
Synthetic Accessibility Score:	7.087
Fsp3:	0.559
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:	-5.226
MDCK Permeability:	1.620411239855457e-05
Pgp-inhibitor:	0.781
Pgp-substrate:	0.955
Human Intestinal Absorption (HIA):	0.283
20% Bioavailability (F20%):	0.693
30% Bioavailability (F30%):	0.732

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.817
Plasma Protein Binding (PPB):	93.61510467529297%
Volume Distribution (VD):	1.452
Pgp-substrate:	6.310196399688721%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.971
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.315
CYP2C9-substrate:	0.181
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.076
CYP3A4-inhibitor:	0.343
CYP3A4-substrate:	0.924

ADMET: Excretion

Clearance (CL):	4.311
Half-life (T1/2):	0.094

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.935
Drug-inuced Liver Injury (DILI):	0.958
AMES Toxicity:	0.432
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.413
Carcinogencity:	0.933
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.98

Download Data

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

Natural Product: NPC233978

Natural Product ID:	NPC233978
*Common Name:**	Scortechinone B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	POTOKMBTWJNFNG-QDASAQQYSA-N
Standard InCHI:	InChI=1S/C34H40O9/c1-16(2)10-11-19-24(35)22-25(36)20-14-32(40-9)15-21-31(7,8)43-33(29(32)39,13-12-17(3)28(37)38)34(20,21)42-27(22)23-26(19)41-18(4)30(23,5)6/h10,12,14,18,21,35H,11,13,15H2,1-9H3,(H,37,38)/b17-12-/t18-,21+,32+,33+,34-/m0/s1
SMILES:	CO[C@]12C=C3C(=O)c4c(O[C@@]53[C@H](C1)C(O[C@@]5(C2=O)C/C=C(C(=O)O)/C)(C)C)c1c(c(c4O)CC=C(C)C)O[C@H](C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL506527
PubChem CID:	44559180
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	=	3380.0	nM	PMID[534210]

☑ 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 NPC233978 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	396
0.1-0.2	1536
0.2-0.3	3126
0.3-0.4	6111
0.4-0.5	10527
0.5-0.6	7433
0.6-0.7	5711
0.7-0.8	7413
0.8-0.85	348
0.85-0.9	41
0.9-0.95	44
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9819	High Similarity	NPC473607
0.9756	High Similarity	NPC169018
0.9701	High Similarity	NPC473729
0.9699	High Similarity	NPC98943
0.9639	High Similarity	NPC162248
0.9581	High Similarity	NPC227275
0.9461	High Similarity	NPC475080
0.9461	High Similarity	NPC476139
0.9461	High Similarity	NPC476229
0.9461	High Similarity	NPC476311
0.9451	High Similarity	NPC189689
0.9345	High Similarity	NPC476152
0.9294	High Similarity	NPC476199
0.9294	High Similarity	NPC476210
0.929	High Similarity	NPC475398
0.9286	High Similarity	NPC476159
0.9281	High Similarity	NPC55422
0.9281	High Similarity	NPC476216
0.9281	High Similarity	NPC75141
0.9281	High Similarity	NPC47634
0.9207	High Similarity	NPC286422
0.9167	High Similarity	NPC41598
0.9167	High Similarity	NPC476146
0.9167	High Similarity	NPC158329
0.9167	High Similarity	NPC40089
0.9162	High Similarity	NPC476255
0.9162	High Similarity	NPC62444
0.9162	High Similarity	NPC475109
0.9112	High Similarity	NPC476196
0.9107	High Similarity	NPC223413
0.9107	High Similarity	NPC193222
0.9102	High Similarity	NPC473908
0.9059	High Similarity	NPC118128
0.9048	High Similarity	NPC476056
0.9042	High Similarity	NPC131578
0.9023	High Similarity	NPC475656
0.9023	High Similarity	NPC475148
0.8982	High Similarity	NPC94796
0.8929	High Similarity	NPC476931
0.8862	High Similarity	NPC43490
0.8862	High Similarity	NPC475107
0.883	High Similarity	NPC63514
0.883	High Similarity	NPC102810
0.8678	High Similarity	NPC469393
0.8671	High Similarity	NPC193698
0.8667	High Similarity	NPC476162
0.8647	High Similarity	NPC475106
0.8631	High Similarity	NPC476930
0.8629	High Similarity	NPC294149
0.8613	High Similarity	NPC54903
0.8613	High Similarity	NPC286074
0.8596	High Similarity	NPC182693
0.8588	High Similarity	NPC476929
0.858	High Similarity	NPC469345
0.8563	High Similarity	NPC313717
0.8563	High Similarity	NPC477670
0.8563	High Similarity	NPC315306
0.8547	High Similarity	NPC316262
0.8547	High Similarity	NPC314653
0.8539	High Similarity	NPC208069
0.8523	High Similarity	NPC86809
0.8523	High Similarity	NPC232412
0.8523	High Similarity	NPC98667
0.8514	High Similarity	NPC472620
0.8514	High Similarity	NPC477529
0.8506	High Similarity	NPC207574
0.8506	High Similarity	NPC297195
0.8506	High Similarity	NPC291795
0.85	High Similarity	NPC197972
0.8497	Intermediate Similarity	NPC17274
0.8497	Intermediate Similarity	NPC85047
0.8497	Intermediate Similarity	NPC469394
0.8497	Intermediate Similarity	NPC120857
0.8475	Intermediate Similarity	NPC324220
0.8475	Intermediate Similarity	NPC312630
0.8471	Intermediate Similarity	NPC125969
0.8462	Intermediate Similarity	NPC477674
0.8457	Intermediate Similarity	NPC251144
0.8457	Intermediate Similarity	NPC241387
0.8452	Intermediate Similarity	NPC477669
0.8427	Intermediate Similarity	NPC5671
0.8427	Intermediate Similarity	NPC477682
0.8427	Intermediate Similarity	NPC477683
0.8421	Intermediate Similarity	NPC313368
0.8409	Intermediate Similarity	NPC473113
0.8402	Intermediate Similarity	NPC477687
0.8402	Intermediate Similarity	NPC477671
0.84	Intermediate Similarity	NPC20734
0.84	Intermediate Similarity	NPC472619
0.84	Intermediate Similarity	NPC473095
0.84	Intermediate Similarity	NPC473096
0.8383	Intermediate Similarity	NPC476509
0.8383	Intermediate Similarity	NPC321387
0.8383	Intermediate Similarity	NPC327059
0.8382	Intermediate Similarity	NPC475055
0.8382	Intermediate Similarity	NPC469395
0.8372	Intermediate Similarity	NPC117985
0.8372	Intermediate Similarity	NPC61382
0.8372	Intermediate Similarity	NPC103816
0.8362	Intermediate Similarity	NPC471969
0.8353	Intermediate Similarity	NPC164427
0.8343	Intermediate Similarity	NPC473094
0.8343	Intermediate Similarity	NPC472622
0.8333	Intermediate Similarity	NPC477672
0.8333	Intermediate Similarity	NPC477673
0.8324	Intermediate Similarity	NPC473022
0.8314	Intermediate Similarity	NPC243701
0.8304	Intermediate Similarity	NPC196448
0.8287	Intermediate Similarity	NPC8927
0.8286	Intermediate Similarity	NPC125465
0.8286	Intermediate Similarity	NPC82330
0.8286	Intermediate Similarity	NPC472621
0.8276	Intermediate Similarity	NPC173587
0.8276	Intermediate Similarity	NPC208120
0.8276	Intermediate Similarity	NPC109180
0.8274	Intermediate Similarity	NPC470908
0.8274	Intermediate Similarity	NPC180351
0.8268	Intermediate Similarity	NPC478050
0.8266	Intermediate Similarity	NPC92589
0.8263	Intermediate Similarity	NPC472345
0.8261	Intermediate Similarity	NPC314672
0.8258	Intermediate Similarity	NPC474276
0.8258	Intermediate Similarity	NPC73899
0.8258	Intermediate Similarity	NPC470942
0.8258	Intermediate Similarity	NPC17105
0.8258	Intermediate Similarity	NPC147363
0.8256	Intermediate Similarity	NPC239118
0.8251	Intermediate Similarity	NPC174486
0.8249	Intermediate Similarity	NPC477571
0.8249	Intermediate Similarity	NPC477572
0.8249	Intermediate Similarity	NPC477573
0.8246	Intermediate Similarity	NPC477675
0.8246	Intermediate Similarity	NPC470625
0.8246	Intermediate Similarity	NPC472050
0.8242	Intermediate Similarity	NPC106700
0.8239	Intermediate Similarity	NPC476459
0.8239	Intermediate Similarity	NPC471975
0.8239	Intermediate Similarity	NPC478060
0.8239	Intermediate Similarity	NPC470374
0.8239	Intermediate Similarity	NPC478059
0.8239	Intermediate Similarity	NPC470377
0.8239	Intermediate Similarity	NPC232936
0.8235	Intermediate Similarity	NPC472799
0.8235	Intermediate Similarity	NPC192189
0.8235	Intermediate Similarity	NPC471695
0.8229	Intermediate Similarity	NPC294722
0.8229	Intermediate Similarity	NPC473766
0.8229	Intermediate Similarity	NPC473753
0.8229	Intermediate Similarity	NPC21016
0.8229	Intermediate Similarity	NPC475979
0.8229	Intermediate Similarity	NPC146584
0.8226	Intermediate Similarity	NPC314020
0.8225	Intermediate Similarity	NPC473131
0.8225	Intermediate Similarity	NPC470675
0.8222	Intermediate Similarity	NPC221820
0.8218	Intermediate Similarity	NPC469849
0.8218	Intermediate Similarity	NPC470940
0.8216	Intermediate Similarity	NPC478034
0.8216	Intermediate Similarity	NPC48474
0.8212	Intermediate Similarity	NPC245975
0.8212	Intermediate Similarity	NPC472665
0.8208	Intermediate Similarity	NPC472055
0.8202	Intermediate Similarity	NPC121333
0.8202	Intermediate Similarity	NPC91650
0.8198	Intermediate Similarity	NPC477403
0.8198	Intermediate Similarity	NPC246466
0.8198	Intermediate Similarity	NPC158542
0.8192	Intermediate Similarity	NPC242395
0.8192	Intermediate Similarity	NPC213416
0.8192	Intermediate Similarity	NPC152477
0.8192	Intermediate Similarity	NPC288813
0.8187	Intermediate Similarity	NPC228209
0.8187	Intermediate Similarity	NPC471456
0.8187	Intermediate Similarity	NPC478221
0.8187	Intermediate Similarity	NPC471116
0.8182	Intermediate Similarity	NPC470197
0.8182	Intermediate Similarity	NPC276565
0.8182	Intermediate Similarity	NPC470196
0.8182	Intermediate Similarity	NPC20237
0.8182	Intermediate Similarity	NPC282474
0.8182	Intermediate Similarity	NPC13481
0.8182	Intermediate Similarity	NPC119589
0.8182	Intermediate Similarity	NPC472344
0.8182	Intermediate Similarity	NPC470195
0.8182	Intermediate Similarity	NPC470193
0.8182	Intermediate Similarity	NPC470198
0.8182	Intermediate Similarity	NPC207575
0.8182	Intermediate Similarity	NPC470200
0.8182	Intermediate Similarity	NPC470194
0.8182	Intermediate Similarity	NPC316274
0.8177	Intermediate Similarity	NPC244903
0.8177	Intermediate Similarity	NPC476273
0.8176	Intermediate Similarity	NPC470353
0.8176	Intermediate Similarity	NPC256141
0.8176	Intermediate Similarity	NPC288534
0.8171	Intermediate Similarity	NPC473313
0.8171	Intermediate Similarity	NPC472581
0.8171	Intermediate Similarity	NPC18100
0.8171	Intermediate Similarity	NPC29055
0.8171	Intermediate Similarity	NPC91288

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 NPC233978 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	349
0.1-0.2	941
0.2-0.3	2038
0.3-0.4	2613
0.4-0.5	1908
0.5-0.6	886
0.6-0.7	280
0.7-0.8	134
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8304	Intermediate Similarity	NPD7075	Discontinued
0.815	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8132	Intermediate Similarity	NPD8434	Phase 2
0.8129	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD2532	Approved
0.8084	Intermediate Similarity	NPD2533	Approved
0.8084	Intermediate Similarity	NPD2534	Approved
0.8081	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7819	Suspended
0.8	Intermediate Similarity	NPD2800	Approved
0.7907	Intermediate Similarity	NPD7411	Suspended
0.7898	Intermediate Similarity	NPD5494	Approved
0.7889	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7861	Intermediate Similarity	NPD6801	Discontinued
0.7861	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD6599	Discontinued
0.7821	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7473	Discontinued
0.7746	Intermediate Similarity	NPD4380	Phase 2
0.7742	Intermediate Similarity	NPD8150	Discontinued
0.7727	Intermediate Similarity	NPD3882	Suspended
0.7727	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5844	Phase 1
0.767	Intermediate Similarity	NPD5402	Approved
0.767	Intermediate Similarity	NPD3817	Phase 2
0.7661	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6959	Discontinued
0.7636	Intermediate Similarity	NPD6651	Approved
0.7633	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD6166	Phase 2
0.7624	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7808	Phase 3
0.7611	Intermediate Similarity	NPD5710	Approved
0.7611	Intermediate Similarity	NPD6232	Discontinued
0.7611	Intermediate Similarity	NPD5711	Approved
0.7609	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD6799	Approved
0.7584	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD3749	Approved
0.7568	Intermediate Similarity	NPD6559	Discontinued
0.7568	Intermediate Similarity	NPD7251	Discontinued
0.7558	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD1934	Approved
0.7556	Intermediate Similarity	NPD1247	Approved
0.7541	Intermediate Similarity	NPD3818	Discontinued
0.7528	Intermediate Similarity	NPD7768	Phase 2
0.7514	Intermediate Similarity	NPD6797	Phase 2
0.7474	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD5403	Approved
0.7459	Intermediate Similarity	NPD7074	Phase 3
0.7444	Intermediate Similarity	NPD919	Approved
0.7416	Intermediate Similarity	NPD2801	Approved
0.7412	Intermediate Similarity	NPD1549	Phase 2
0.7412	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7054	Approved
0.7394	Intermediate Similarity	NPD8313	Approved
0.7394	Intermediate Similarity	NPD8312	Approved
0.7386	Intermediate Similarity	NPD3226	Approved
0.7374	Intermediate Similarity	NPD7435	Discontinued
0.7366	Intermediate Similarity	NPD7472	Approved
0.7356	Intermediate Similarity	NPD5401	Approved
0.7353	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD3751	Discontinued
0.7351	Intermediate Similarity	NPD7228	Approved
0.7348	Intermediate Similarity	NPD6234	Discontinued
0.7337	Intermediate Similarity	NPD2403	Approved
0.7333	Intermediate Similarity	NPD4965	Approved
0.7333	Intermediate Similarity	NPD4967	Phase 2
0.7333	Intermediate Similarity	NPD4966	Approved
0.7326	Intermediate Similarity	NPD3750	Approved
0.7318	Intermediate Similarity	NPD1465	Phase 2
0.7294	Intermediate Similarity	NPD6100	Approved
0.7294	Intermediate Similarity	NPD6099	Approved
0.7273	Intermediate Similarity	NPD920	Approved
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7874	Approved
0.7225	Intermediate Similarity	NPD8366	Approved
0.7225	Intermediate Similarity	NPD4628	Phase 3
0.7225	Intermediate Similarity	NPD7907	Approved
0.7216	Intermediate Similarity	NPD1512	Approved
0.72	Intermediate Similarity	NPD7697	Approved
0.72	Intermediate Similarity	NPD7698	Approved
0.72	Intermediate Similarity	NPD7696	Phase 3
0.7196	Intermediate Similarity	NPD6765	Approved
0.7196	Intermediate Similarity	NPD6764	Approved
0.7193	Intermediate Similarity	NPD2796	Approved
0.7192	Intermediate Similarity	NPD8151	Discontinued
0.7189	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD8491	Approved
0.7168	Intermediate Similarity	NPD1243	Approved
0.7167	Intermediate Similarity	NPD37	Approved
0.7166	Intermediate Similarity	NPD7799	Discontinued
0.7164	Intermediate Similarity	NPD7871	Phase 2
0.7164	Intermediate Similarity	NPD7870	Phase 2
0.716	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5124	Phase 1
0.7159	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD2346	Discontinued
0.7136	Intermediate Similarity	NPD6779	Approved
0.7136	Intermediate Similarity	NPD6777	Approved
0.7136	Intermediate Similarity	NPD6776	Approved
0.7136	Intermediate Similarity	NPD6778	Approved
0.7136	Intermediate Similarity	NPD6781	Approved
0.7136	Intermediate Similarity	NPD6780	Approved
0.7136	Intermediate Similarity	NPD6782	Approved
0.7136	Intermediate Similarity	NPD8469	Approved
0.7135	Intermediate Similarity	NPD3787	Discontinued
0.7135	Intermediate Similarity	NPD1510	Phase 2
0.7127	Intermediate Similarity	NPD5761	Phase 2
0.7127	Intermediate Similarity	NPD5760	Phase 2
0.7102	Intermediate Similarity	NPD1511	Approved
0.7097	Intermediate Similarity	NPD3926	Phase 2
0.7095	Intermediate Similarity	NPD7458	Discontinued
0.7093	Intermediate Similarity	NPD2935	Discontinued
0.7083	Intermediate Similarity	NPD8407	Phase 2
0.7081	Intermediate Similarity	NPD8127	Discontinued
0.7079	Intermediate Similarity	NPD8320	Phase 1
0.7079	Intermediate Similarity	NPD8319	Approved
0.7062	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7701	Phase 2
0.7053	Intermediate Similarity	NPD5953	Discontinued
0.705	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD6785	Approved
0.7047	Intermediate Similarity	NPD6784	Approved
0.7045	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7801	Approved
0.7039	Intermediate Similarity	NPD7783	Phase 2
0.7039	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7286	Phase 2
0.7035	Intermediate Similarity	NPD3748	Approved
0.7035	Intermediate Similarity	NPD2799	Discontinued
0.7035	Intermediate Similarity	NPD7700	Phase 2
0.7035	Intermediate Similarity	NPD7699	Phase 2
0.7033	Intermediate Similarity	NPD8404	Phase 2
0.7018	Intermediate Similarity	NPD1607	Approved
0.7016	Intermediate Similarity	NPD8368	Discontinued
0.7016	Intermediate Similarity	NPD7240	Approved
0.7	Intermediate Similarity	NPD8285	Discontinued
0.7	Intermediate Similarity	NPD1240	Approved
0.6994	Remote Similarity	NPD1551	Phase 2
0.6989	Remote Similarity	NPD7199	Phase 2
0.6984	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6534	Approved
0.697	Remote Similarity	NPD6535	Approved
0.6967	Remote Similarity	NPD4665	Approved
0.6967	Remote Similarity	NPD4111	Phase 1
0.6952	Remote Similarity	NPD7229	Phase 3
0.6949	Remote Similarity	NPD7236	Approved
0.6932	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7685	Pre-registration
0.6916	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD6190	Approved
0.6891	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2313	Discontinued
0.6882	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.686	Remote Similarity	NPD230	Phase 1
0.686	Remote Similarity	NPD6355	Discontinued
0.6857	Remote Similarity	NPD1471	Phase 3
0.6853	Remote Similarity	NPD8435	Approved
0.6853	Remote Similarity	NPD8361	Approved
0.6853	Remote Similarity	NPD4287	Approved
0.6853	Remote Similarity	NPD8360	Approved
0.6851	Remote Similarity	NPD7239	Suspended
0.6839	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6836	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6273	Approved
0.6831	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD7390	Discontinued
0.6814	Remote Similarity	NPD6823	Phase 2
0.6798	Remote Similarity	NPD4107	Approved
0.678	Remote Similarity	NPD7497	Discontinued
0.6763	Remote Similarity	NPD447	Suspended
0.6763	Remote Similarity	NPD7584	Approved
0.6761	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6005	Phase 3
0.6761	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD6002	Phase 3
0.6761	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD2344	Approved
0.6761	Remote Similarity	NPD6004	Phase 3
0.6757	Remote Similarity	NPD8455	Phase 2
0.6742	Remote Similarity	NPD8166	Discontinued
0.6742	Remote Similarity	NPD7003	Approved
0.6733	Remote Similarity	NPD8485	Approved
0.6732	Remote Similarity	NPD3057	Approved
0.6727	Remote Similarity	NPD8067	Phase 3
0.672	Remote Similarity	NPD5353	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