NPASS Compound

Structure

CID121888 OpenBabel06191715472D 47 55 0 0 1 0 0 0 0 0999 V2000 -0.8423 4.2593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1453 0.3719 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9708 -0.0915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7069 -0.3005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1801 -1.1202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0993 1.4024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2868 1.8773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3366 -2.2482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8197 -3.0623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1763 -2.2142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6398 -1.3888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6521 2.8408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0204 2.8469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4428 1.4297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1271 0.4028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6299 0.0218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7604 -1.9399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2767 -0.0049 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8385 3.3145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7604 -0.3005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4428 0.4911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7069 -1.9399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0942 0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4692 1.4111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2297 -2.2255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6528 1.8897 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0060 1.9001 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8000 -1.4228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7663 -3.0510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6299 1.8990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2625 0.0179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2872 -1.1202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4641 0.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8171 0.4911 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8171 1.4297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8346 1.4221 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7466 -1.4114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1567 -0.5747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8231 0.4704 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1801 -2.7595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9113 -0.0164 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2494 -3.8651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6299 2.8455 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3614 -0.9234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6460 0.0024 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 -2.2101 -0.5860 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 38 1 0 0 0 0 3 38 1 0 0 0 0 4 5 2 0 0 0 0 4 20 1 0 0 0 0 5 22 1 0 0 0 0 6 7 2 0 0 0 0 6 23 1 0 0 0 0 7 24 1 0 0 0 0 8 9 2 0 0 0 0 8 28 1 0 0 0 0 9 29 1 0 0 0 0 10 11 2 0 0 0 0 10 25 1 0 0 0 0 11 38 1 0 0 0 0 12 19 1 0 0 0 0 13 19 2 0 0 0 0 14 21 2 0 0 0 0 14 30 1 0 0 0 0 15 20 1 0 0 0 0 15 31 2 0 0 0 0 16 21 1 0 0 0 0 16 34 2 0 0 0 0 17 22 2 0 0 0 0 17 32 1 0 0 0 0 18 23 2 0 0 0 0 18 33 1 0 0 0 0 20 32 2 0 0 0 0 21 31 1 0 0 0 0 22 40 1 0 0 0 0 23 41 1 0 0 0 0 24 26 1 0 0 0 0 24 33 2 0 0 0 0 25 29 2 0 0 0 0 25 37 1 0 0 0 0 26 12 1 6 0 0 0 26 36 1 0 0 0 0 27 13 1 6 0 0 0 27 35 1 0 0 0 0 27 36 1 0 0 0 0 28 37 2 0 0 0 0 29 42 1 0 0 0 0 30 35 2 0 0 0 0 30 43 1 0 0 0 0 31 44 1 0 0 0 0 32 44 1 0 0 0 0 33 45 1 0 0 0 0 34 35 1 0 0 0 0 34 46 1 0 0 0 0 36 39 1 1 0 0 0 37 47 1 0 0 0 0 38 47 1 0 0 0 0 39 28 1 1 0 0 0 39 45 1 0 0 0 0 39 46 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	628.21
Volume:	636.867
LogP:	8.325
LogD:	4.991
LogS:	-1.627
# Rotatable Bonds:	2
TPSA:	121.75
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	9
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.144
Synthetic Accessibility Score:	4.874
Fsp3:	0.231
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:	-5.302
MDCK Permeability:	1.3437775123747997e-05
Pgp-inhibitor:	0.642
Pgp-substrate:	0.469
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.951
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	100.08588409423828%
Volume Distribution (VD):	0.728
Pgp-substrate:	1.000716209411621%

ADMET: Metabolism

CYP1A2-inhibitor:	0.261
CYP1A2-substrate:	0.412
CYP2C19-inhibitor:	0.963
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.927
CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.796
CYP2D6-substrate:	0.374
CYP3A4-inhibitor:	0.764
CYP3A4-substrate:	0.429

ADMET: Excretion

Clearance (CL):	5.376
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.317
Human Hepatotoxicity (H-HT):	0.846
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.467
Rat Oral Acute Toxicity:	0.833
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.935
Carcinogencity:	0.934
Eye Corrosion:	0.003
Eye Irritation:	0.842
Respiratory Toxicity:	0.621

Download Data

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

Natural Product: NPC121888

Natural Product ID:	NPC121888
*Common Name:**	Sorocenol G
IUPAC Name:	n.a.
Synonyms:	Sorocenol G
Standard InCHIKey:	GOBAQYCCUYZMJY-HGLYATPPSA-N
Standard InCHI:	InChI=1S/C39H32O8/c1-19-12-26-24-7-6-23(41)18-33(24)45-39(28-8-9-29(42)25-10-11-38(2,3)47-37(25)28)36(26)27(13-19)35-30(43)14-21(16-34(35)46-39)31-15-20-4-5-22(40)17-32(20)44-31/h4-11,13-18,26-27,36,40-43H,12H2,1-3H3/t26-,27+,36-,39-/m0/s1
SMILES:	CC1=C[C@@H]2c3c(O)cc(cc3O[C@]3([C@H]2[C@@H](C1)c1ccc(cc1O3)O)c1ccc(c2c1OC(C)(C)C=C2)O)c1oc2c(c1)ccc(c2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454537
PubChem CID:	25135702
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO8299	Sorocea muriculata	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[18847244]
NPO8299	Sorocea muriculata	Species	Moraceae	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
MIC	1
Others	1

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	1500.0	nM	PMID[495206]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4000.0	nM	PMID[495206]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	=	31.8	uM	PMID[495206]

☑ 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 NPC121888 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	464
0.1-0.2	1886
0.2-0.3	3904
0.3-0.4	10071
0.4-0.5	8717
0.5-0.6	4011
0.6-0.7	6056
0.7-0.8	5998
0.8-0.85	1466
0.85-0.9	113
0.9-0.95	6
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9879	High Similarity	NPC101991
0.9758	High Similarity	NPC24748
0.9758	High Similarity	NPC59491
0.9515	High Similarity	NPC253730
0.9515	High Similarity	NPC286230
0.9394	High Similarity	NPC169471
0.9333	High Similarity	NPC159508
0.9064	High Similarity	NPC17105
0.9064	High Similarity	NPC147363
0.9064	High Similarity	NPC474276
0.9064	High Similarity	NPC73899
0.9048	High Similarity	NPC473010
0.8988	High Similarity	NPC473009
0.897	High Similarity	NPC54830
0.897	High Similarity	NPC137100
0.897	High Similarity	NPC56049
0.8929	High Similarity	NPC473012
0.8902	High Similarity	NPC300657
0.8882	High Similarity	NPC251336
0.8869	High Similarity	NPC312273
0.8869	High Similarity	NPC301256
0.8848	High Similarity	NPC472462
0.8848	High Similarity	NPC72370
0.883	High Similarity	NPC292233
0.8817	High Similarity	NPC477528
0.881	High Similarity	NPC312993
0.881	High Similarity	NPC195136
0.881	High Similarity	NPC121647
0.8802	High Similarity	NPC65504
0.8802	High Similarity	NPC268360
0.8786	High Similarity	NPC477529
0.8765	High Similarity	NPC38591
0.8764	High Similarity	NPC87583
0.8757	High Similarity	NPC273467
0.8757	High Similarity	NPC189552
0.875	High Similarity	NPC51760
0.875	High Similarity	NPC177650
0.875	High Similarity	NPC105584
0.8728	High Similarity	NPC8704
0.8728	High Similarity	NPC287884
0.8706	High Similarity	NPC15374
0.8698	High Similarity	NPC226462
0.8698	High Similarity	NPC186325
0.8698	High Similarity	NPC98023
0.8693	High Similarity	NPC478000
0.869	High Similarity	NPC1796
0.869	High Similarity	NPC96342
0.869	High Similarity	NPC164110
0.869	High Similarity	NPC212967
0.869	High Similarity	NPC246647
0.8683	High Similarity	NPC150908
0.8683	High Similarity	NPC297531
0.8683	High Similarity	NPC213936
0.8683	High Similarity	NPC215203
0.8683	High Similarity	NPC275575
0.8683	High Similarity	NPC100049
0.8683	High Similarity	NPC158027
0.8683	High Similarity	NPC14606
0.8683	High Similarity	NPC205026
0.8683	High Similarity	NPC265624
0.8683	High Similarity	NPC159707
0.8683	High Similarity	NPC99199
0.8683	High Similarity	NPC52611
0.8683	High Similarity	NPC121649
0.8683	High Similarity	NPC248739
0.8683	High Similarity	NPC186227
0.8671	High Similarity	NPC470206
0.8671	High Similarity	NPC470207
0.8667	High Similarity	NPC230713
0.8667	High Similarity	NPC167576
0.8667	High Similarity	NPC78335
0.8655	High Similarity	NPC155640
0.8647	High Similarity	NPC472261
0.8647	High Similarity	NPC175513
0.8644	High Similarity	NPC299149
0.8644	High Similarity	NPC277710
0.8644	High Similarity	NPC153578
0.8644	High Similarity	NPC114257
0.8639	High Similarity	NPC51247
0.8639	High Similarity	NPC15815
0.8639	High Similarity	NPC18699
0.8639	High Similarity	NPC474373
0.8639	High Similarity	NPC55443
0.8631	High Similarity	NPC69531
0.8631	High Similarity	NPC32867
0.8631	High Similarity	NPC180924
0.8629	High Similarity	NPC168789
0.8623	High Similarity	NPC213608
0.8623	High Similarity	NPC303485
0.8623	High Similarity	NPC71061
0.8623	High Similarity	NPC235333
0.8623	High Similarity	NPC72425
0.8623	High Similarity	NPC1477
0.8623	High Similarity	NPC290830
0.8623	High Similarity	NPC194593
0.8621	High Similarity	NPC477571
0.8621	High Similarity	NPC477573
0.8621	High Similarity	NPC477572
0.8614	High Similarity	NPC67322
0.8614	High Similarity	NPC138299
0.8614	High Similarity	NPC170169
0.8614	High Similarity	NPC222713
0.8614	High Similarity	NPC149085
0.8614	High Similarity	NPC111112
0.8613	High Similarity	NPC76647
0.8611	High Similarity	NPC73929
0.8611	High Similarity	NPC139683
0.8611	High Similarity	NPC47905
0.8606	High Similarity	NPC178202
0.8606	High Similarity	NPC221868
0.8606	High Similarity	NPC37208
0.8605	High Similarity	NPC469664
0.8596	High Similarity	NPC473011
0.8588	High Similarity	NPC42965
0.8588	High Similarity	NPC472060
0.8588	High Similarity	NPC470342
0.8588	High Similarity	NPC472052
0.858	High Similarity	NPC475184
0.858	High Similarity	NPC271741
0.858	High Similarity	NPC257166
0.858	High Similarity	NPC287789
0.8571	High Similarity	NPC148938
0.8571	High Similarity	NPC300668
0.8571	High Similarity	NPC66441
0.8571	High Similarity	NPC254351
0.8571	High Similarity	NPC37253
0.8571	High Similarity	NPC182555
0.8571	High Similarity	NPC79375
0.8571	High Similarity	NPC134171
0.8563	High Similarity	NPC5871
0.8563	High Similarity	NPC142527
0.8563	High Similarity	NPC53252
0.8563	High Similarity	NPC142308
0.8556	High Similarity	NPC221140
0.8556	High Similarity	NPC229817
0.8556	High Similarity	NPC475352
0.8556	High Similarity	NPC473686
0.8556	High Similarity	NPC475220
0.8556	High Similarity	NPC304322
0.8547	High Similarity	NPC473717
0.8547	High Similarity	NPC475662
0.8547	High Similarity	NPC473631
0.8547	High Similarity	NPC293227
0.8547	High Similarity	NPC132111
0.8545	High Similarity	NPC272194
0.8538	High Similarity	NPC18380
0.8538	High Similarity	NPC137232
0.8531	High Similarity	NPC475233
0.8531	High Similarity	NPC475246
0.8531	High Similarity	NPC46958
0.8529	High Similarity	NPC40583
0.8529	High Similarity	NPC472877
0.8529	High Similarity	NPC226287
0.8529	High Similarity	NPC295090
0.8529	High Similarity	NPC90497
0.8529	High Similarity	NPC244750
0.8523	High Similarity	NPC470336
0.8523	High Similarity	NPC213052
0.8523	High Similarity	NPC470335
0.8521	High Similarity	NPC309648
0.8521	High Similarity	NPC61112
0.8521	High Similarity	NPC198489
0.8512	High Similarity	NPC324447
0.8512	High Similarity	NPC329844
0.8512	High Similarity	NPC121568
0.8503	High Similarity	NPC193976
0.8503	High Similarity	NPC23668
0.8497	Intermediate Similarity	NPC474591
0.8494	Intermediate Similarity	NPC291746
0.8494	Intermediate Similarity	NPC288840
0.8494	Intermediate Similarity	NPC226644
0.8494	Intermediate Similarity	NPC37226
0.8492	Intermediate Similarity	NPC97523
0.8492	Intermediate Similarity	NPC475161
0.8492	Intermediate Similarity	NPC477860
0.8488	Intermediate Similarity	NPC310603
0.8488	Intermediate Similarity	NPC477239
0.8488	Intermediate Similarity	NPC3448
0.8483	Intermediate Similarity	NPC5671
0.848	Intermediate Similarity	NPC292863
0.848	Intermediate Similarity	NPC260296
0.848	Intermediate Similarity	NPC184326
0.848	Intermediate Similarity	NPC115432
0.848	Intermediate Similarity	NPC172687
0.8475	Intermediate Similarity	NPC227906
0.8475	Intermediate Similarity	NPC3718
0.8471	Intermediate Similarity	NPC324358
0.8471	Intermediate Similarity	NPC322459
0.8471	Intermediate Similarity	NPC208258
0.8471	Intermediate Similarity	NPC318527
0.8471	Intermediate Similarity	NPC323627
0.847	Intermediate Similarity	NPC264302
0.8466	Intermediate Similarity	NPC477836
0.8466	Intermediate Similarity	NPC223375
0.8466	Intermediate Similarity	NPC475825
0.8466	Intermediate Similarity	NPC478002
0.8462	Intermediate Similarity	NPC66508
0.8462	Intermediate Similarity	NPC198490
0.8462	Intermediate Similarity	NPC258474
0.8462	Intermediate Similarity	NPC201227

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 NPC121888 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	993
0.2-0.3	1648
0.3-0.4	2756
0.4-0.5	2016
0.5-0.6	895
0.6-0.7	268
0.7-0.8	161
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8647	High Similarity	NPD6959	Discontinued
0.8471	Intermediate Similarity	NPD3749	Approved
0.8418	Intermediate Similarity	NPD6559	Discontinued
0.8391	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8353	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8249	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8222	Intermediate Similarity	NPD8313	Approved
0.8222	Intermediate Similarity	NPD8312	Approved
0.8198	Intermediate Similarity	NPD7768	Phase 2
0.8187	Intermediate Similarity	NPD7819	Suspended
0.8136	Intermediate Similarity	NPD7473	Discontinued
0.807	Intermediate Similarity	NPD7411	Suspended
0.8046	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8045	Intermediate Similarity	NPD7054	Approved
0.8036	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8011	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7472	Approved
0.7989	Intermediate Similarity	NPD3818	Discontinued
0.7976	Intermediate Similarity	NPD7390	Discontinued
0.7967	Intermediate Similarity	NPD7808	Phase 3
0.7966	Intermediate Similarity	NPD6232	Discontinued
0.7955	Intermediate Similarity	NPD5494	Approved
0.7912	Intermediate Similarity	NPD7251	Discontinued
0.7907	Intermediate Similarity	NPD4380	Phase 2
0.7877	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD6166	Phase 2
0.7877	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6797	Phase 2
0.7841	Intermediate Similarity	NPD7075	Discontinued
0.7766	Intermediate Similarity	NPD8151	Discontinued
0.776	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7747	Intermediate Similarity	NPD5844	Phase 1
0.7746	Intermediate Similarity	NPD3226	Approved
0.7738	Intermediate Similarity	NPD2800	Approved
0.7738	Intermediate Similarity	NPD1243	Approved
0.7733	Intermediate Similarity	NPD920	Approved
0.7725	Intermediate Similarity	NPD2344	Approved
0.7719	Intermediate Similarity	NPD2534	Approved
0.7719	Intermediate Similarity	NPD2533	Approved
0.7719	Intermediate Similarity	NPD2532	Approved
0.7692	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD7698	Approved
0.7692	Intermediate Similarity	NPD7697	Approved
0.7692	Intermediate Similarity	NPD3750	Approved
0.7692	Intermediate Similarity	NPD7696	Phase 3
0.7684	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD1549	Phase 2
0.767	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD2801	Approved
0.7661	Intermediate Similarity	NPD1511	Approved
0.7653	Intermediate Similarity	NPD7871	Phase 2
0.7653	Intermediate Similarity	NPD7870	Phase 2
0.7619	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD1934	Approved
0.7605	Intermediate Similarity	NPD1510	Phase 2
0.76	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7783	Phase 2
0.759	Intermediate Similarity	NPD1607	Approved
0.7584	Intermediate Similarity	NPD3882	Suspended
0.7581	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD1512	Approved
0.7571	Intermediate Similarity	NPD8455	Phase 2
0.756	Intermediate Similarity	NPD6099	Approved
0.756	Intermediate Similarity	NPD6100	Approved
0.756	Intermediate Similarity	NPD2796	Approved
0.7553	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD2309	Approved
0.7543	Intermediate Similarity	NPD7458	Discontinued
0.7538	Intermediate Similarity	NPD6780	Approved
0.7538	Intermediate Similarity	NPD6781	Approved
0.7538	Intermediate Similarity	NPD6779	Approved
0.7538	Intermediate Similarity	NPD6782	Approved
0.7538	Intermediate Similarity	NPD7701	Phase 2
0.7538	Intermediate Similarity	NPD6776	Approved
0.7538	Intermediate Similarity	NPD6777	Approved
0.7538	Intermediate Similarity	NPD6778	Approved
0.7527	Intermediate Similarity	NPD3926	Phase 2
0.7526	Intermediate Similarity	NPD4287	Approved
0.7515	Intermediate Similarity	NPD2346	Discontinued
0.7514	Intermediate Similarity	NPD6801	Discontinued
0.7513	Intermediate Similarity	NPD7435	Discontinued
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3751	Discontinued
0.7472	Intermediate Similarity	NPD1465	Phase 2
0.7471	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1240	Approved
0.7456	Intermediate Similarity	NPD5408	Approved
0.7456	Intermediate Similarity	NPD5406	Approved
0.7456	Intermediate Similarity	NPD5404	Approved
0.7456	Intermediate Similarity	NPD5405	Approved
0.7436	Intermediate Similarity	NPD7700	Phase 2
0.7436	Intermediate Similarity	NPD7699	Phase 2
0.743	Intermediate Similarity	NPD3817	Phase 2
0.7429	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD7801	Approved
0.7421	Intermediate Similarity	NPD8150	Discontinued
0.7421	Intermediate Similarity	NPD8434	Phase 2
0.7418	Intermediate Similarity	NPD1247	Approved
0.7414	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7228	Approved
0.7403	Intermediate Similarity	NPD919	Approved
0.7401	Intermediate Similarity	NPD6599	Discontinued
0.7396	Intermediate Similarity	NPD2799	Discontinued
0.7396	Intermediate Similarity	NPD3748	Approved
0.7387	Intermediate Similarity	NPD8320	Phase 1
0.7387	Intermediate Similarity	NPD8319	Approved
0.7377	Intermediate Similarity	NPD7229	Phase 3
0.7377	Intermediate Similarity	NPD3787	Discontinued
0.7376	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD7874	Approved
0.7374	Intermediate Similarity	NPD6823	Phase 2
0.7353	Intermediate Similarity	NPD2935	Discontinued
0.7345	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5402	Approved
0.7312	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5710	Approved
0.7283	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5711	Approved
0.7283	Intermediate Similarity	NPD7003	Approved
0.7282	Intermediate Similarity	NPD6535	Approved
0.7282	Intermediate Similarity	NPD6534	Approved
0.7278	Intermediate Similarity	NPD6651	Approved
0.7257	Intermediate Similarity	NPD6799	Approved
0.7251	Intermediate Similarity	NPD1551	Phase 2
0.7246	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD2313	Discontinued
0.7228	Intermediate Similarity	NPD7199	Phase 2
0.7222	Intermediate Similarity	NPD37	Approved
0.7213	Intermediate Similarity	NPD6234	Discontinued
0.7212	Intermediate Similarity	NPD2798	Approved
0.7209	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD4966	Approved
0.7198	Intermediate Similarity	NPD4965	Approved
0.7198	Intermediate Similarity	NPD4967	Phase 2
0.7196	Intermediate Similarity	NPD5953	Discontinued
0.7186	Intermediate Similarity	NPD4625	Phase 3
0.7182	Intermediate Similarity	NPD5761	Phase 2
0.7182	Intermediate Similarity	NPD5760	Phase 2
0.7181	Intermediate Similarity	NPD7286	Phase 2
0.7158	Intermediate Similarity	NPD7685	Pre-registration
0.7151	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7584	Approved
0.7135	Intermediate Similarity	NPD5403	Approved
0.7128	Intermediate Similarity	NPD7177	Discontinued
0.7126	Intermediate Similarity	NPD4908	Phase 1
0.7121	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7240	Approved
0.7062	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD2296	Approved
0.7041	Intermediate Similarity	NPD3764	Approved
0.7041	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4749	Approved
0.7022	Intermediate Similarity	NPD5401	Approved
0.702	Intermediate Similarity	NPD4360	Phase 2
0.702	Intermediate Similarity	NPD4363	Phase 3
0.7011	Intermediate Similarity	NPD1471	Phase 3
0.6994	Remote Similarity	NPD4308	Phase 3
0.6989	Remote Similarity	NPD4628	Phase 3
0.697	Remote Similarity	NPD6213	Phase 3
0.697	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6212	Phase 3
0.6965	Remote Similarity	NPD8285	Discontinued
0.6959	Remote Similarity	NPD943	Approved
0.6948	Remote Similarity	NPD8366	Approved
0.6944	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD8059	Phase 3
0.6941	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3268	Approved
0.6931	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD7680	Approved
0.69	Remote Similarity	NPD4361	Phase 2
0.69	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD6273	Approved
0.6885	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD4288	Approved
0.6849	Remote Similarity	NPD8067	Phase 3
0.6845	Remote Similarity	NPD2797	Approved
0.6845	Remote Similarity	NPD1203	Approved
0.6845	Remote Similarity	NPD1470	Approved
0.6839	Remote Similarity	NPD7097	Phase 1
0.6825	Remote Similarity	NPD7930	Approved
0.6824	Remote Similarity	NPD6832	Phase 2
0.6821	Remote Similarity	NPD5124	Phase 1
0.6821	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.682	Remote Similarity	NPD8491	Approved
0.68	Remote Similarity	NPD7033	Discontinued
0.6779	Remote Similarity	NPD7585	Approved
0.6772	Remote Similarity	NPD8127	Discontinued

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