NPASS Compound

Structure

NPC471687 OpenBabel07101719162D 34 37 0 0 1 0 0 0 0 0999 V2000 0.8432 -5.3553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8598 0.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8861 0.8432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3301 1.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3564 1.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5560 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -4.3816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6865 -3.8947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2162 -0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6865 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.8947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0594 0.0000 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 0.4868 0.0000 Br 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -4.3816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -4.3816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0429 -2.3038 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 12 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 24 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 25 1 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 22 1 0 0 0 0 14 21 1 0 0 0 0 14 26 1 1 0 0 0 15 29 1 0 0 0 0 16 23 1 0 0 0 0 16 25 1 1 0 0 0 17 23 1 0 0 0 0 17 27 1 1 0 0 0 18 24 1 0 0 0 0 18 28 1 1 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 30 1 0 0 0 0 21 31 2 0 0 0 0 22 26 1 0 0 0 0 22 32 2 0 0 0 0 24 34 1 0 0 0 0 25 6 1 1 0 0 0 25 33 1 0 0 0 0 26 11 1 6 0 0 0 26 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	600.07
Volume:	502.153
LogP:	5.37
LogD:	3.453
LogS:	-4.357
# Rotatable Bonds:	2
TPSA:	104.06
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.39
Synthetic Accessibility Score:	5.19
Fsp3:	0.692
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.775
MDCK Permeability:	1.5143369637371507e-05
Pgp-inhibitor:	0.963
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.106
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.372

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.647
Plasma Protein Binding (PPB):	98.37264251708984%
Volume Distribution (VD):	1.075
Pgp-substrate:	2.332937002182007%

ADMET: Metabolism

CYP1A2-inhibitor:	0.261
CYP1A2-substrate:	0.735
CYP2C19-inhibitor:	0.573
CYP2C19-substrate:	0.624
CYP2C9-inhibitor:	0.937
CYP2C9-substrate:	0.853
CYP2D6-inhibitor:	0.124
CYP2D6-substrate:	0.398
CYP3A4-inhibitor:	0.693
CYP3A4-substrate:	0.805

ADMET: Excretion

Clearance (CL):	3.8
Half-life (T1/2):	0.036

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.38
Drug-inuced Liver Injury (DILI):	0.326
AMES Toxicity:	0.169
Rat Oral Acute Toxicity:	0.436
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.26
Carcinogencity:	0.85
Eye Corrosion:	0.003
Eye Irritation:	0.106
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC471687

Natural Product ID:	NPC471687
*Common Name:**	Napyradiomycin Cnq525.600
IUPAC Name:	(3R,4aS,10aR)-3-bromo-10a-[[(1S,3S,6S)-3-bromo-6-hydroxy-2,2,6-trimethylcyclohexyl]methyl]-6,8-dihydroxy-2,2,7-trimethyl-4,4a-dihydro-3H-benzo[g]chromene-5,10-dione
Synonyms:
Standard InCHIKey:	GQSXTXLHELBDSQ-CJWPEDLKSA-N
Standard InCHI:	InChI=1S/C26H34Br2O6/c1-12-15(29)9-13-19(20(12)30)21(31)14-10-18(28)24(4,5)34-26(14,22(13)32)11-16-23(2,3)17(27)7-8-25(16,6)33/h9,14,16-18,29-30,33H,7-8,10-11H2,1-6H3/t14-,16+,17+,18-,25+,26-/m1/s1
SMILES:	O=C1c2c(O)c(C)c(cc2C(=O)[C@]2([C@@H]1C[C@@H](Br)C(O2)(C)C)C[C@@H]1[C@@](C)(O)CC[C@@H](C1(C)C)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3104842
PubChem CID:	76321116
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans [CHEMONTID:0001641] Naphthopyranones

*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
NPO32475	actinomycete sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24328269]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	49000.0	nM	PMID[457134]

☑ 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 NPC471687 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	481
0.1-0.2	1873
0.2-0.3	3806
0.3-0.4	9847
0.4-0.5	10340
0.5-0.6	6287
0.6-0.7	7884
0.7-0.8	2157
0.8-0.85	19
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8698	High Similarity	NPC158699
0.8614	High Similarity	NPC471685
0.8563	High Similarity	NPC301846
0.8547	High Similarity	NPC471686
0.8462	Intermediate Similarity	NPC108948
0.8353	Intermediate Similarity	NPC184518
0.8343	Intermediate Similarity	NPC311679
0.8284	Intermediate Similarity	NPC73544
0.828	Intermediate Similarity	NPC169452
0.828	Intermediate Similarity	NPC181560
0.8235	Intermediate Similarity	NPC131078
0.8217	Intermediate Similarity	NPC138099
0.8217	Intermediate Similarity	NPC242994
0.8205	Intermediate Similarity	NPC471905
0.8187	Intermediate Similarity	NPC471906
0.8176	Intermediate Similarity	NPC316262
0.8176	Intermediate Similarity	NPC193555
0.8176	Intermediate Similarity	NPC314653
0.8166	Intermediate Similarity	NPC475106
0.8141	Intermediate Similarity	NPC254847
0.8141	Intermediate Similarity	NPC191976
0.8113	Intermediate Similarity	NPC246638
0.8101	Intermediate Similarity	NPC143438
0.8089	Intermediate Similarity	NPC53414
0.8089	Intermediate Similarity	NPC53206
0.8086	Intermediate Similarity	NPC470570
0.8063	Intermediate Similarity	NPC308572
0.8063	Intermediate Similarity	NPC135524
0.8063	Intermediate Similarity	NPC474961
0.8057	Intermediate Similarity	NPC471684
0.8037	Intermediate Similarity	NPC37709
0.8036	Intermediate Similarity	NPC272196
0.8036	Intermediate Similarity	NPC201127
0.8036	Intermediate Similarity	NPC474637
0.8025	Intermediate Similarity	NPC34482
0.8023	Intermediate Similarity	NPC125465
0.8	Intermediate Similarity	NPC110810
0.8	Intermediate Similarity	NPC204045
0.8	Intermediate Similarity	NPC305845
0.7989	Intermediate Similarity	NPC313717
0.7989	Intermediate Similarity	NPC315306
0.7988	Intermediate Similarity	NPC472617
0.7987	Intermediate Similarity	NPC190457
0.7977	Intermediate Similarity	NPC470566
0.7975	Intermediate Similarity	NPC53001
0.7964	Intermediate Similarity	NPC472211
0.7963	Intermediate Similarity	NPC48762
0.7963	Intermediate Similarity	NPC193703
0.7963	Intermediate Similarity	NPC21599
0.7963	Intermediate Similarity	NPC244691
0.7952	Intermediate Similarity	NPC305965
0.7949	Intermediate Similarity	NPC267205
0.7941	Intermediate Similarity	NPC472618
0.7941	Intermediate Similarity	NPC313368
0.7931	Intermediate Similarity	NPC470567
0.7931	Intermediate Similarity	NPC54903
0.7931	Intermediate Similarity	NPC286074
0.7927	Intermediate Similarity	NPC245584
0.7927	Intermediate Similarity	NPC190648
0.7927	Intermediate Similarity	NPC126767
0.7927	Intermediate Similarity	NPC289042
0.7927	Intermediate Similarity	NPC118027
0.7927	Intermediate Similarity	NPC56433
0.7927	Intermediate Similarity	NPC312929
0.7925	Intermediate Similarity	NPC87723
0.7922	Intermediate Similarity	NPC303910
0.7914	Intermediate Similarity	NPC470673
0.7914	Intermediate Similarity	NPC117716
0.7914	Intermediate Similarity	NPC470674
0.7914	Intermediate Similarity	NPC474630
0.7914	Intermediate Similarity	NPC28632
0.7914	Intermediate Similarity	NPC12402
0.7911	Intermediate Similarity	NPC474311
0.7907	Intermediate Similarity	NPC100849
0.7904	Intermediate Similarity	NPC40356
0.7904	Intermediate Similarity	NPC142527
0.7904	Intermediate Similarity	NPC154683
0.7901	Intermediate Similarity	NPC451542
0.7901	Intermediate Similarity	NPC293545
0.7901	Intermediate Similarity	NPC271451
0.7901	Intermediate Similarity	NPC313047
0.7901	Intermediate Similarity	NPC174905
0.7901	Intermediate Similarity	NPC474203
0.7901	Intermediate Similarity	NPC295712
0.7898	Intermediate Similarity	NPC282780
0.7898	Intermediate Similarity	NPC44437
0.7898	Intermediate Similarity	NPC166480
0.7895	Intermediate Similarity	NPC103816
0.7895	Intermediate Similarity	NPC61382
0.7895	Intermediate Similarity	NPC219686
0.7892	Intermediate Similarity	NPC470568
0.7892	Intermediate Similarity	NPC147735
0.7892	Intermediate Similarity	NPC294646
0.7888	Intermediate Similarity	NPC290550
0.7879	Intermediate Similarity	NPC94781
0.7879	Intermediate Similarity	NPC142846
0.7871	Intermediate Similarity	NPC108129
0.787	Intermediate Similarity	NPC4547
0.7866	Intermediate Similarity	NPC85393
0.7866	Intermediate Similarity	NPC110882
0.7866	Intermediate Similarity	NPC473135
0.7866	Intermediate Similarity	NPC271944
0.7866	Intermediate Similarity	NPC470676
0.7866	Intermediate Similarity	NPC136878
0.7866	Intermediate Similarity	NPC473132
0.7857	Intermediate Similarity	NPC474824
0.7857	Intermediate Similarity	NPC182921
0.7857	Intermediate Similarity	NPC218870
0.7857	Intermediate Similarity	NPC214632
0.7857	Intermediate Similarity	NPC470408
0.7853	Intermediate Similarity	NPC227841
0.7848	Intermediate Similarity	NPC249272
0.7844	Intermediate Similarity	NPC478148
0.7844	Intermediate Similarity	NPC470569
0.7841	Intermediate Similarity	NPC118128
0.7831	Intermediate Similarity	NPC474310
0.7831	Intermediate Similarity	NPC120171
0.7831	Intermediate Similarity	NPC329933
0.7824	Intermediate Similarity	NPC158542
0.7818	Intermediate Similarity	NPC34802
0.7818	Intermediate Similarity	NPC5568
0.7816	Intermediate Similarity	NPC120857
0.7816	Intermediate Similarity	NPC17274
0.7816	Intermediate Similarity	NPC476056
0.7816	Intermediate Similarity	NPC85047
0.7812	Intermediate Similarity	NPC13715
0.7811	Intermediate Similarity	NPC226656
0.7811	Intermediate Similarity	NPC275575
0.7811	Intermediate Similarity	NPC66508
0.7798	Intermediate Similarity	NPC45934
0.7798	Intermediate Similarity	NPC470353
0.7797	Intermediate Similarity	NPC469393
0.7791	Intermediate Similarity	NPC471682
0.7791	Intermediate Similarity	NPC100242
0.7785	Intermediate Similarity	NPC12070
0.7785	Intermediate Similarity	NPC202225
0.7785	Intermediate Similarity	NPC270899
0.7784	Intermediate Similarity	NPC205766
0.7784	Intermediate Similarity	NPC255641
0.7784	Intermediate Similarity	NPC290954
0.7784	Intermediate Similarity	NPC315520
0.7784	Intermediate Similarity	NPC24435
0.7778	Intermediate Similarity	NPC324736
0.7778	Intermediate Similarity	NPC228654
0.7778	Intermediate Similarity	NPC92079
0.7778	Intermediate Similarity	NPC239118
0.7771	Intermediate Similarity	NPC193222
0.7771	Intermediate Similarity	NPC112816
0.7771	Intermediate Similarity	NPC76647
0.7765	Intermediate Similarity	NPC192587
0.7765	Intermediate Similarity	NPC470354
0.7765	Intermediate Similarity	NPC474861
0.7765	Intermediate Similarity	NPC470352
0.7765	Intermediate Similarity	NPC470334
0.7764	Intermediate Similarity	NPC103337
0.7764	Intermediate Similarity	NPC114620
0.7759	Intermediate Similarity	NPC472049
0.7758	Intermediate Similarity	NPC285122
0.7758	Intermediate Similarity	NPC143685
0.7751	Intermediate Similarity	NPC178964
0.7751	Intermediate Similarity	NPC95842
0.7751	Intermediate Similarity	NPC280530
0.7751	Intermediate Similarity	NPC329844
0.7746	Intermediate Similarity	NPC94796
0.7746	Intermediate Similarity	NPC470694
0.7746	Intermediate Similarity	NPC473022
0.7744	Intermediate Similarity	NPC10764
0.7744	Intermediate Similarity	NPC29932
0.7744	Intermediate Similarity	NPC19896
0.7738	Intermediate Similarity	NPC473131
0.7738	Intermediate Similarity	NPC230848
0.7738	Intermediate Similarity	NPC470675
0.7738	Intermediate Similarity	NPC474417
0.7738	Intermediate Similarity	NPC149526
0.7736	Intermediate Similarity	NPC283088
0.7736	Intermediate Similarity	NPC290803
0.7733	Intermediate Similarity	NPC472052
0.7733	Intermediate Similarity	NPC472060
0.7733	Intermediate Similarity	NPC470342
0.7733	Intermediate Similarity	NPC284495
0.773	Intermediate Similarity	NPC257644
0.773	Intermediate Similarity	NPC291078
0.773	Intermediate Similarity	NPC73061
0.7727	Intermediate Similarity	NPC20734
0.7725	Intermediate Similarity	NPC52931
0.7725	Intermediate Similarity	NPC65775
0.7725	Intermediate Similarity	NPC477221
0.7725	Intermediate Similarity	NPC280753
0.7725	Intermediate Similarity	NPC10027
0.7725	Intermediate Similarity	NPC44378
0.7725	Intermediate Similarity	NPC80370
0.7725	Intermediate Similarity	NPC269420
0.7722	Intermediate Similarity	NPC37299
0.7722	Intermediate Similarity	NPC114183
0.7722	Intermediate Similarity	NPC180261
0.7719	Intermediate Similarity	NPC281137
0.7719	Intermediate Similarity	NPC263483
0.7719	Intermediate Similarity	NPC282390
0.7716	Intermediate Similarity	NPC156872
0.7714	Intermediate Similarity	NPC62444

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 NPC471687 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	413
0.1-0.2	1045
0.2-0.3	1921
0.3-0.4	3155
0.4-0.5	1777
0.5-0.6	590
0.6-0.7	232
0.7-0.8	17
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
0.8141	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD7390	Discontinued
0.7586	Intermediate Similarity	NPD6959	Discontinued
0.7514	Intermediate Similarity	NPD7473	Discontinued
0.7381	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD6232	Discontinued
0.7341	Intermediate Similarity	NPD7819	Suspended
0.7326	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1470	Approved
0.7317	Intermediate Similarity	NPD6100	Approved
0.7317	Intermediate Similarity	NPD6099	Approved
0.7317	Intermediate Similarity	NPD5406	Approved
0.7317	Intermediate Similarity	NPD5405	Approved
0.7317	Intermediate Similarity	NPD5404	Approved
0.7317	Intermediate Similarity	NPD5408	Approved
0.7299	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2534	Approved
0.7278	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD2533	Approved
0.7278	Intermediate Similarity	NPD2532	Approved
0.7256	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7075	Discontinued
0.7204	Intermediate Similarity	NPD8150	Discontinued
0.7186	Intermediate Similarity	NPD2800	Approved
0.7168	Intermediate Similarity	NPD4380	Phase 2
0.7143	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD3749	Approved
0.7117	Intermediate Similarity	NPD943	Approved
0.711	Intermediate Similarity	NPD3226	Approved
0.7076	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD1201	Approved
0.7069	Intermediate Similarity	NPD6599	Discontinued
0.7037	Intermediate Similarity	NPD4287	Approved
0.703	Intermediate Similarity	NPD6651	Approved
0.703	Intermediate Similarity	NPD1607	Approved
0.7029	Intermediate Similarity	NPD7411	Suspended
0.7005	Intermediate Similarity	NPD8319	Approved
0.7005	Intermediate Similarity	NPD8320	Phase 1
0.6979	Remote Similarity	NPD6535	Approved
0.6979	Remote Similarity	NPD6534	Approved
0.6978	Remote Similarity	NPD6166	Phase 2
0.6978	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD3882	Suspended
0.6959	Remote Similarity	NPD7699	Phase 2
0.6959	Remote Similarity	NPD3300	Phase 2
0.6959	Remote Similarity	NPD7700	Phase 2
0.6957	Remote Similarity	NPD5844	Phase 1
0.6957	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7435	Discontinued
0.6946	Remote Similarity	NPD1510	Phase 2
0.6944	Remote Similarity	NPD5494	Approved
0.6936	Remote Similarity	NPD1512	Approved
0.6923	Remote Similarity	NPD1549	Phase 2
0.6909	Remote Similarity	NPD1240	Approved
0.6893	Remote Similarity	NPD6801	Discontinued
0.6893	Remote Similarity	NPD1934	Approved
0.6888	Remote Similarity	NPD6780	Approved
0.6888	Remote Similarity	NPD6776	Approved
0.6888	Remote Similarity	NPD6777	Approved
0.6888	Remote Similarity	NPD6781	Approved
0.6888	Remote Similarity	NPD6778	Approved
0.6888	Remote Similarity	NPD6779	Approved
0.6888	Remote Similarity	NPD6782	Approved
0.6885	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD7768	Phase 2
0.6869	Remote Similarity	NPD7698	Approved
0.6869	Remote Similarity	NPD7697	Approved
0.6869	Remote Similarity	NPD7696	Phase 3
0.6868	Remote Similarity	NPD5711	Approved
0.6868	Remote Similarity	NPD5710	Approved
0.6864	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD2346	Discontinued
0.6854	Remote Similarity	NPD2801	Approved
0.6845	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD3750	Approved
0.6834	Remote Similarity	NPD7870	Phase 2
0.6834	Remote Similarity	NPD7871	Phase 2
0.6821	Remote Similarity	NPD1511	Approved
0.6816	Remote Similarity	NPD4288	Approved
0.6778	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.676	Remote Similarity	NPD1465	Phase 2
0.6755	Remote Similarity	NPD7251	Discontinued
0.6749	Remote Similarity	NPD7874	Approved
0.6749	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.674	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7701	Phase 2
0.673	Remote Similarity	NPD3019	Approved
0.6724	Remote Similarity	NPD6799	Approved
0.6722	Remote Similarity	NPD3817	Phase 2
0.672	Remote Similarity	NPD3751	Discontinued
0.672	Remote Similarity	NPD7808	Phase 3
0.6716	Remote Similarity	NPD7801	Approved
0.6706	Remote Similarity	NPD2935	Discontinued
0.6706	Remote Similarity	NPD2796	Approved
0.6702	Remote Similarity	NPD6797	Phase 2
0.67	Remote Similarity	NPD8151	Discontinued
0.6688	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3764	Approved
0.6684	Remote Similarity	NPD8312	Approved
0.6684	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6559	Discontinued
0.6649	Remote Similarity	NPD7074	Phase 3
0.6647	Remote Similarity	NPD7003	Approved
0.6634	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.663	Remote Similarity	NPD5402	Approved
0.6629	Remote Similarity	NPD7458	Discontinued
0.6625	Remote Similarity	NPD2932	Approved
0.6615	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6596	Remote Similarity	NPD7054	Approved
0.6596	Remote Similarity	NPD6020	Phase 2
0.658	Remote Similarity	NPD8434	Phase 2
0.6571	Remote Similarity	NPD7236	Approved
0.6568	Remote Similarity	NPD230	Phase 1
0.6561	Remote Similarity	NPD7472	Approved
0.6552	Remote Similarity	NPD8166	Discontinued
0.655	Remote Similarity	NPD3748	Approved
0.655	Remote Similarity	NPD2799	Discontinued
0.6543	Remote Similarity	NPD3818	Discontinued
0.6538	Remote Similarity	NPD2296	Approved
0.6536	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD4625	Phase 3
0.6514	Remote Similarity	NPD6190	Approved
0.6508	Remote Similarity	NPD7286	Phase 2
0.6505	Remote Similarity	NPD3787	Discontinued
0.6497	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6212	Phase 3
0.6497	Remote Similarity	NPD6213	Phase 3
0.6497	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6485	Remote Similarity	NPD1164	Approved
0.6485	Remote Similarity	NPD6823	Phase 2
0.6484	Remote Similarity	NPD5760	Phase 2
0.6484	Remote Similarity	NPD5761	Phase 2
0.648	Remote Similarity	NPD7239	Suspended
0.6474	Remote Similarity	NPD2344	Approved
0.6474	Remote Similarity	NPD1471	Phase 3
0.6471	Remote Similarity	NPD3926	Phase 2
0.6457	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1247	Approved
0.645	Remote Similarity	NPD6663	Approved
0.6448	Remote Similarity	NPD8438	Clinical (unspecified phase)
0.644	Remote Similarity	NPD5953	Discontinued
0.6432	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6425	Remote Similarity	NPD5403	Approved
0.6425	Remote Similarity	NPD920	Approved
0.6417	Remote Similarity	NPD7229	Phase 3
0.6416	Remote Similarity	NPD1551	Phase 2
0.6407	Remote Similarity	NPD5736	Approved
0.6402	Remote Similarity	NPD9269	Phase 2
0.64	Remote Similarity	NPD1243	Approved
0.6391	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.638	Remote Similarity	NPD3023	Approved
0.638	Remote Similarity	NPD3026	Approved
0.6373	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6368	Remote Similarity	NPD7799	Discontinued
0.6368	Remote Similarity	NPD7228	Approved
0.6364	Remote Similarity	NPD4628	Phase 3
0.6364	Remote Similarity	NPD4749	Approved
0.6358	Remote Similarity	NPD9268	Approved
0.6358	Remote Similarity	NPD3025	Approved
0.6358	Remote Similarity	NPD3024	Approved
0.6353	Remote Similarity	NPD7961	Discontinued
0.6349	Remote Similarity	NPD2403	Approved
0.6346	Remote Similarity	NPD4750	Phase 3
0.6344	Remote Similarity	NPD919	Approved
0.6344	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6234	Discontinued
0.6339	Remote Similarity	NPD37	Approved
0.6328	Remote Similarity	NPD2309	Approved
0.6324	Remote Similarity	NPD4966	Approved
0.6324	Remote Similarity	NPD4967	Phase 2
0.6324	Remote Similarity	NPD4965	Approved
0.6321	Remote Similarity	NPD5027	Approved
0.6321	Remote Similarity	NPD5031	Approved
0.6321	Remote Similarity	NPD5029	Approved
0.6318	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7783	Phase 2
0.6316	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD5401	Approved
0.63	Remote Similarity	NPD4360	Phase 2
0.63	Remote Similarity	NPD4363	Phase 3
0.6294	Remote Similarity	NPD2313	Discontinued
0.6289	Remote Similarity	NPD4954	Approved
0.6289	Remote Similarity	NPD5028	Approved
0.6289	Remote Similarity	NPD5026	Approved
0.6289	Remote Similarity	NPD36	Approved
0.6289	Remote Similarity	NPD4955	Approved
0.6289	Remote Similarity	NPD5034	Approved
0.6278	Remote Similarity	NPD6273	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