NPASS Compound

Structure

NPC471600 OpenBabel07101718202D 29 32 0 0 1 0 0 0 0 0999 V2000 1.8615 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7945 -0.2289 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3347 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3706 4.5932 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8706 3.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 2.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7366 2.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9955 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2738 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4686 1.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3890 1.5374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9955 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9683 0.3345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4686 0.2272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 1.2029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 1.7272 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.0259 1.1031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6369 0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 1.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 -0.2728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 3.7272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7366 1.2272 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.7366 0.2272 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.9269 1.5370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 2.7272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6026 -1.2728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9955 4.2272 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 7 2 0 0 0 0 6 22 1 0 0 0 0 7 23 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 14 2 0 0 0 0 9 19 1 0 0 0 0 10 15 2 0 0 0 0 10 20 1 0 0 0 0 11 16 1 0 0 0 0 11 18 2 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 19 2 0 0 0 0 17 23 1 0 0 0 0 18 25 1 0 0 0 0 19 29 1 0 0 0 0 20 23 1 0 0 0 0 20 26 2 0 0 0 0 21 24 1 0 0 0 0 21 27 2 0 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	394.18
Volume:	412.294
LogP:	3.399
LogD:	2.917
LogS:	-3.877
# Rotatable Bonds:	2
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.748
Synthetic Accessibility Score:	5.465
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.763
MDCK Permeability:	1.8491800801712088e-05
Pgp-inhibitor:	0.15
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.091
20% Bioavailability (F20%):	0.144
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	90.26431274414062%
Volume Distribution (VD):	1.287
Pgp-substrate:	8.592814445495605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.063
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.583
CYP2C19-substrate:	0.815
CYP2C9-inhibitor:	0.585
CYP2C9-substrate:	0.843
CYP2D6-inhibitor:	0.56
CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.648
CYP3A4-substrate:	0.808

ADMET: Excretion

Clearance (CL):	3.703
Half-life (T1/2):	0.173

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.471
Drug-inuced Liver Injury (DILI):	0.141
AMES Toxicity:	0.335
Rat Oral Acute Toxicity:	0.879
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.054
Carcinogencity:	0.758
Eye Corrosion:	0.003
Eye Irritation:	0.061
Respiratory Toxicity:	0.925

Download Data

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

Natural Product: NPC471600

Natural Product ID:	NPC471600
*Common Name:**	ZJBCEAAFFNQWIJ-VOTSOKGWSA-N
IUPAC Name:	n.a.
Synonyms:	Rac-Acremine G
Standard InCHIKey:	ZJBCEAAFFNQWIJ-VOTSOKGWSA-N
Standard InCHI:	InChI=1S/C24H26O5/c1-13-8-17-16-11-18(25)14(2)9-19(16)29-24(12-13)21(27)15(3)10-20(26)23(17,24)7-6-22(4,5)28/h6-11,17,25,28H,12H2,1-5H3/b7-6+
SMILES:	CC1=CC2c3cc(O)c(cc3OC3(C1)C2(/C=C/C(O)(C)C)C(=O)C=C(C3=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL274744
PubChem CID:	44448248
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO32554	acremonium byssoides a20	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[18154270]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	48000.0	nM	PMID[468117]
NPT1095	Organism	Plasmopara viticola	Plasmopara viticola	Inhibition	=	72.5	%	PMID[468117]

☑ 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 NPC471600 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	394
0.1-0.2	1538
0.2-0.3	3577
0.3-0.4	8720
0.4-0.5	10196
0.5-0.6	4902
0.6-0.7	9746
0.7-0.8	3575
0.8-0.85	46
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9927	High Similarity	NPC316691
0.8472	Intermediate Similarity	NPC474610
0.8429	Intermediate Similarity	NPC201419
0.8354	Intermediate Similarity	NPC475106
0.8345	Intermediate Similarity	NPC194847
0.8345	Intermediate Similarity	NPC21797
0.8333	Intermediate Similarity	NPC477210
0.8322	Intermediate Similarity	NPC118253
0.831	Intermediate Similarity	NPC196621
0.8299	Intermediate Similarity	NPC79372
0.8291	Intermediate Similarity	NPC476929
0.8288	Intermediate Similarity	NPC301341
0.8276	Intermediate Similarity	NPC22222
0.8276	Intermediate Similarity	NPC281513
0.8252	Intermediate Similarity	NPC474143
0.8252	Intermediate Similarity	NPC474246
0.8231	Intermediate Similarity	NPC475104
0.8217	Intermediate Similarity	NPC67197
0.8207	Intermediate Similarity	NPC27394
0.82	Intermediate Similarity	NPC474599
0.8194	Intermediate Similarity	NPC251549
0.8194	Intermediate Similarity	NPC312560
0.8187	Intermediate Similarity	NPC476931
0.8182	Intermediate Similarity	NPC475880
0.8176	Intermediate Similarity	NPC477408
0.8176	Intermediate Similarity	NPC76312
0.817	Intermediate Similarity	NPC474556
0.8163	Intermediate Similarity	NPC284184
0.8163	Intermediate Similarity	NPC98804
0.8151	Intermediate Similarity	NPC22644
0.8146	Intermediate Similarity	NPC477409
0.8143	Intermediate Similarity	NPC248557
0.8138	Intermediate Similarity	NPC171968
0.8133	Intermediate Similarity	NPC201297
0.8125	Intermediate Similarity	NPC141549
0.8112	Intermediate Similarity	NPC206028
0.8112	Intermediate Similarity	NPC59654
0.8112	Intermediate Similarity	NPC271832
0.8108	Intermediate Similarity	NPC265335
0.8102	Intermediate Similarity	NPC51341
0.8095	Intermediate Similarity	NPC471670
0.8095	Intermediate Similarity	NPC475549
0.8089	Intermediate Similarity	NPC3898
0.8086	Intermediate Similarity	NPC476056
0.8077	Intermediate Similarity	NPC142527
0.8065	Intermediate Similarity	NPC475718
0.8056	Intermediate Similarity	NPC278787
0.8056	Intermediate Similarity	NPC253488
0.8054	Intermediate Similarity	NPC470407
0.8041	Intermediate Similarity	NPC156888
0.8041	Intermediate Similarity	NPC477534
0.8041	Intermediate Similarity	NPC470722
0.8041	Intermediate Similarity	NPC470721
0.8041	Intermediate Similarity	NPC6100
0.8038	Intermediate Similarity	NPC469507
0.8037	Intermediate Similarity	NPC193222
0.8025	Intermediate Similarity	NPC314653
0.8025	Intermediate Similarity	NPC316262
0.8014	Intermediate Similarity	NPC470871
0.8013	Intermediate Similarity	NPC305965
0.8013	Intermediate Similarity	NPC329493
0.8013	Intermediate Similarity	NPC474154
0.8	Intermediate Similarity	NPC43490
0.8	Intermediate Similarity	NPC475044
0.8	Intermediate Similarity	NPC313368
0.8	Intermediate Similarity	NPC475107
0.8	Intermediate Similarity	NPC475063
0.8	Intermediate Similarity	NPC205360
0.7988	Intermediate Similarity	NPC286074
0.7988	Intermediate Similarity	NPC54903
0.7987	Intermediate Similarity	NPC201127
0.7987	Intermediate Similarity	NPC252208
0.7975	Intermediate Similarity	NPC326910
0.7975	Intermediate Similarity	NPC62444
0.7975	Intermediate Similarity	NPC478159
0.7975	Intermediate Similarity	NPC478161
0.7975	Intermediate Similarity	NPC275575
0.7974	Intermediate Similarity	NPC474630
0.7972	Intermediate Similarity	NPC477211
0.7972	Intermediate Similarity	NPC319422
0.7972	Intermediate Similarity	NPC477212
0.7972	Intermediate Similarity	NPC95034
0.7972	Intermediate Similarity	NPC477214
0.7972	Intermediate Similarity	NPC142087
0.7971	Intermediate Similarity	NPC471449
0.7963	Intermediate Similarity	NPC469395
0.7962	Intermediate Similarity	NPC45934
0.7961	Intermediate Similarity	NPC1534
0.795	Intermediate Similarity	NPC61382
0.795	Intermediate Similarity	NPC103816
0.7949	Intermediate Similarity	NPC101957
0.7949	Intermediate Similarity	NPC120105
0.7947	Intermediate Similarity	NPC124365
0.7935	Intermediate Similarity	NPC37135
0.7935	Intermediate Similarity	NPC474107
0.7935	Intermediate Similarity	NPC186397
0.7933	Intermediate Similarity	NPC475012
0.7933	Intermediate Similarity	NPC475045
0.7931	Intermediate Similarity	NPC7569
0.7931	Intermediate Similarity	NPC470725
0.7925	Intermediate Similarity	NPC470354
0.7925	Intermediate Similarity	NPC470352
0.7922	Intermediate Similarity	NPC196114
0.7922	Intermediate Similarity	NPC211565
0.7922	Intermediate Similarity	NPC329678
0.7919	Intermediate Similarity	NPC118366
0.7919	Intermediate Similarity	NPC471542
0.7917	Intermediate Similarity	NPC47288
0.7911	Intermediate Similarity	NPC95842
0.7911	Intermediate Similarity	NPC178964
0.7911	Intermediate Similarity	NPC280530
0.7908	Intermediate Similarity	NPC89664
0.7908	Intermediate Similarity	NPC274085
0.7908	Intermediate Similarity	NPC169942
0.7908	Intermediate Similarity	NPC475813
0.7908	Intermediate Similarity	NPC473813
0.7908	Intermediate Similarity	NPC473812
0.7901	Intermediate Similarity	NPC94796
0.7898	Intermediate Similarity	NPC81474
0.7895	Intermediate Similarity	NPC69755
0.7888	Intermediate Similarity	NPC284495
0.7888	Intermediate Similarity	NPC472618
0.7887	Intermediate Similarity	NPC474237
0.7887	Intermediate Similarity	NPC147896
0.7885	Intermediate Similarity	NPC223988
0.7885	Intermediate Similarity	NPC266499
0.7885	Intermediate Similarity	NPC269420
0.7877	Intermediate Similarity	NPC324488
0.7877	Intermediate Similarity	NPC258073
0.7875	Intermediate Similarity	NPC272196
0.7875	Intermediate Similarity	NPC282390
0.7875	Intermediate Similarity	NPC196448
0.7875	Intermediate Similarity	NPC281137
0.7872	Intermediate Similarity	NPC49441
0.7871	Intermediate Similarity	NPC478163
0.7867	Intermediate Similarity	NPC475028
0.7867	Intermediate Similarity	NPC474943
0.7867	Intermediate Similarity	NPC476025
0.7867	Intermediate Similarity	NPC475005
0.7867	Intermediate Similarity	NPC173980
0.7866	Intermediate Similarity	NPC85047
0.7866	Intermediate Similarity	NPC120857
0.7866	Intermediate Similarity	NPC17274
0.7857	Intermediate Similarity	NPC472447
0.7857	Intermediate Similarity	NPC470674
0.7857	Intermediate Similarity	NPC117716
0.7857	Intermediate Similarity	NPC472446
0.7857	Intermediate Similarity	NPC470673
0.7853	Intermediate Similarity	NPC159508
0.7852	Intermediate Similarity	NPC232996
0.7848	Intermediate Similarity	NPC470353
0.7844	Intermediate Similarity	NPC475080
0.7844	Intermediate Similarity	NPC469393
0.7843	Intermediate Similarity	NPC204469
0.7843	Intermediate Similarity	NPC53016
0.784	Intermediate Similarity	NPC472275
0.7834	Intermediate Similarity	NPC227122
0.7834	Intermediate Similarity	NPC150928
0.7832	Intermediate Similarity	NPC477213
0.7832	Intermediate Similarity	NPC224657
0.7831	Intermediate Similarity	NPC313717
0.7831	Intermediate Similarity	NPC315306
0.7826	Intermediate Similarity	NPC185258
0.7826	Intermediate Similarity	NPC172770
0.7821	Intermediate Similarity	NPC296869
0.7817	Intermediate Similarity	NPC135062
0.7815	Intermediate Similarity	NPC476191
0.7812	Intermediate Similarity	NPC4547
0.7812	Intermediate Similarity	NPC288353
0.7812	Intermediate Similarity	NPC164244
0.7812	Intermediate Similarity	NPC471968
0.7808	Intermediate Similarity	NPC198305
0.7806	Intermediate Similarity	NPC473135
0.7806	Intermediate Similarity	NPC477955
0.7806	Intermediate Similarity	NPC60389
0.7806	Intermediate Similarity	NPC470676
0.7806	Intermediate Similarity	NPC300540
0.7806	Intermediate Similarity	NPC473132
0.7801	Intermediate Similarity	NPC168707
0.7801	Intermediate Similarity	NPC48623
0.78	Intermediate Similarity	NPC130976
0.78	Intermediate Similarity	NPC290601
0.7799	Intermediate Similarity	NPC305710
0.7793	Intermediate Similarity	NPC237225
0.7793	Intermediate Similarity	NPC81261
0.7793	Intermediate Similarity	NPC176590
0.7791	Intermediate Similarity	NPC470694
0.7791	Intermediate Similarity	NPC473022
0.7785	Intermediate Similarity	NPC473131
0.7785	Intermediate Similarity	NPC144283
0.7785	Intermediate Similarity	NPC470675
0.7784	Intermediate Similarity	NPC118128
0.7778	Intermediate Similarity	NPC306765
0.7771	Intermediate Similarity	NPC20734
0.7771	Intermediate Similarity	NPC226578
0.7771	Intermediate Similarity	NPC471114
0.7771	Intermediate Similarity	NPC474052
0.777	Intermediate Similarity	NPC211352
0.777	Intermediate Similarity	NPC477536
0.777	Intermediate Similarity	NPC59459

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 NPC471600 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	365
0.1-0.2	959
0.2-0.3	1585
0.3-0.4	2616
0.4-0.5	2037
0.5-0.6	1080
0.6-0.7	441
0.7-0.8	64
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8188	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8041	Intermediate Similarity	NPD6099	Approved
0.8041	Intermediate Similarity	NPD6100	Approved
0.7867	Intermediate Similarity	NPD2346	Discontinued
0.7681	Intermediate Similarity	NPD6671	Approved
0.7658	Intermediate Similarity	NPD3226	Approved
0.7628	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3268	Approved
0.7566	Intermediate Similarity	NPD2935	Discontinued
0.7516	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD2799	Discontinued
0.7466	Intermediate Similarity	NPD2797	Approved
0.745	Intermediate Similarity	NPD2313	Discontinued
0.745	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD4749	Approved
0.7415	Intermediate Similarity	NPD2798	Approved
0.7405	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD1471	Phase 3
0.7397	Intermediate Similarity	NPD6696	Suspended
0.7396	Intermediate Similarity	NPD3751	Discontinued
0.7391	Intermediate Similarity	NPD6599	Discontinued
0.7389	Intermediate Similarity	NPD3300	Phase 2
0.7383	Intermediate Similarity	NPD7095	Approved
0.7376	Intermediate Similarity	NPD7340	Approved
0.7362	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD3496	Discontinued
0.7345	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7075	Discontinued
0.7329	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD7458	Discontinued
0.7325	Intermediate Similarity	NPD2309	Approved
0.7317	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2800	Approved
0.7305	Intermediate Similarity	NPD6959	Discontinued
0.7292	Intermediate Similarity	NPD1778	Approved
0.7286	Intermediate Similarity	NPD1398	Phase 1
0.7273	Intermediate Similarity	NPD4308	Phase 3
0.7261	Intermediate Similarity	NPD7003	Approved
0.7261	Intermediate Similarity	NPD4628	Phase 3
0.726	Intermediate Similarity	NPD1608	Approved
0.726	Intermediate Similarity	NPD3972	Approved
0.7256	Intermediate Similarity	NPD7819	Suspended
0.7256	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2801	Approved
0.725	Intermediate Similarity	NPD1512	Approved
0.7246	Intermediate Similarity	NPD5494	Approved
0.7244	Intermediate Similarity	NPD1549	Phase 2
0.7237	Intermediate Similarity	NPD4060	Phase 1
0.723	Intermediate Similarity	NPD3267	Approved
0.723	Intermediate Similarity	NPD3266	Approved
0.7219	Intermediate Similarity	NPD411	Approved
0.7216	Intermediate Similarity	NPD8434	Phase 2
0.7212	Intermediate Similarity	NPD5402	Approved
0.7197	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD6844	Discontinued
0.7195	Intermediate Similarity	NPD1934	Approved
0.7192	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD6355	Discontinued
0.7179	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD4380	Phase 2
0.7176	Intermediate Similarity	NPD6166	Phase 2
0.7176	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2932	Approved
0.7171	Intermediate Similarity	NPD8032	Phase 2
0.7169	Intermediate Similarity	NPD3882	Suspended
0.7152	Intermediate Similarity	NPD8166	Discontinued
0.7152	Intermediate Similarity	NPD3750	Approved
0.7152	Intermediate Similarity	NPD4625	Phase 3
0.7151	Intermediate Similarity	NPD5844	Phase 1
0.7143	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD1607	Approved
0.7143	Intermediate Similarity	NPD6273	Approved
0.7134	Intermediate Similarity	NPD7411	Suspended
0.7133	Intermediate Similarity	NPD2861	Phase 2
0.7125	Intermediate Similarity	NPD1511	Approved
0.7119	Intermediate Similarity	NPD8150	Discontinued
0.7114	Intermediate Similarity	NPD1203	Approved
0.7114	Intermediate Similarity	NPD1470	Approved
0.7105	Intermediate Similarity	NPD6798	Discontinued
0.7078	Intermediate Similarity	NPD447	Suspended
0.7075	Intermediate Similarity	NPD1611	Approved
0.7073	Intermediate Similarity	NPD7028	Phase 2
0.707	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3787	Discontinued
0.7059	Intermediate Similarity	NPD6233	Phase 2
0.7055	Intermediate Similarity	NPD3019	Approved
0.7055	Intermediate Similarity	NPD4626	Approved
0.7055	Intermediate Similarity	NPD17	Approved
0.7052	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1510	Phase 2
0.7051	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7033	Discontinued
0.7042	Intermediate Similarity	NPD1241	Discontinued
0.7035	Intermediate Similarity	NPD7473	Discontinued
0.7025	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3749	Approved
0.7019	Intermediate Similarity	NPD6799	Approved
0.7014	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1240	Approved
0.7013	Intermediate Similarity	NPD4307	Phase 2
0.7006	Intermediate Similarity	NPD2796	Approved
0.7006	Intermediate Similarity	NPD3817	Phase 2
0.6993	Remote Similarity	NPD7985	Registered
0.6993	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6801	Discontinued
0.6986	Remote Similarity	NPD1651	Approved
0.6986	Remote Similarity	NPD5585	Approved
0.6977	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2532	Approved
0.6975	Remote Similarity	NPD2534	Approved
0.6975	Remote Similarity	NPD2533	Approved
0.6973	Remote Similarity	NPD6779	Approved
0.6973	Remote Similarity	NPD6778	Approved
0.6973	Remote Similarity	NPD6780	Approved
0.6973	Remote Similarity	NPD6776	Approved
0.6973	Remote Similarity	NPD6782	Approved
0.6973	Remote Similarity	NPD6781	Approved
0.6973	Remote Similarity	NPD6777	Approved
0.6971	Remote Similarity	NPD6797	Phase 2
0.6966	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7644	Approved
0.6959	Remote Similarity	NPD6232	Discontinued
0.6959	Remote Similarity	NPD1201	Approved
0.6959	Remote Similarity	NPD1535	Discovery
0.6957	Remote Similarity	NPD7236	Approved
0.6952	Remote Similarity	NPD7435	Discontinued
0.6951	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD8313	Approved
0.6949	Remote Similarity	NPD8312	Approved
0.6944	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD1283	Approved
0.6933	Remote Similarity	NPD3225	Approved
0.6932	Remote Similarity	NPD7251	Discontinued
0.6923	Remote Similarity	NPD6651	Approved
0.6913	Remote Similarity	NPD1481	Phase 2
0.6901	Remote Similarity	NPD8127	Discontinued
0.6899	Remote Similarity	NPD1551	Phase 2
0.6894	Remote Similarity	NPD2354	Approved
0.6893	Remote Similarity	NPD7808	Phase 3
0.689	Remote Similarity	NPD5403	Approved
0.6883	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7097	Phase 1
0.6871	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD5691	Approved
0.6864	Remote Similarity	NPD7768	Phase 2
0.6864	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6832	Phase 2
0.6863	Remote Similarity	NPD4908	Phase 1
0.6862	Remote Similarity	NPD7698	Approved
0.6862	Remote Similarity	NPD7696	Phase 3
0.6862	Remote Similarity	NPD7697	Approved
0.6859	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5762	Approved
0.6855	Remote Similarity	NPD5763	Approved
0.6848	Remote Similarity	NPD7239	Suspended
0.6845	Remote Similarity	NPD5760	Phase 2
0.6845	Remote Similarity	NPD5761	Phase 2
0.6842	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3446	Phase 1
0.6836	Remote Similarity	NPD6559	Discontinued
0.6836	Remote Similarity	NPD6764	Approved
0.6836	Remote Similarity	NPD6765	Approved
0.6835	Remote Similarity	NPD3748	Approved
0.6832	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD4110	Phase 3
0.6829	Remote Similarity	NPD5049	Phase 3
0.6825	Remote Similarity	NPD7871	Phase 2
0.6825	Remote Similarity	NPD7870	Phase 2
0.6818	Remote Similarity	NPD7074	Phase 3
0.6813	Remote Similarity	NPD2424	Discontinued
0.681	Remote Similarity	NPD7390	Discontinued
0.6805	Remote Similarity	NPD2296	Approved
0.6802	Remote Similarity	NPD1247	Approved
0.68	Remote Similarity	NPD7177	Discontinued
0.6795	Remote Similarity	NPD2979	Phase 3
0.6795	Remote Similarity	NPD4140	Approved
0.6788	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7577	Discontinued
0.6774	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1578	Phase 2
0.6768	Remote Similarity	NPD5401	Approved
0.6761	Remote Similarity	NPD7054	Approved
0.6755	Remote Similarity	NPD4359	Approved
0.6755	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6002	Phase 3
0.675	Remote Similarity	NPD2353	Approved
0.675	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.675	Remote Similarity	NPD6005	Phase 3
0.675	Remote Similarity	NPD2355	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