NPASS Compound

Structure

NPC470207 OpenBabel07101719252D 31 35 0 0 1 0 0 0 0 0999 V2000 5.8259 -2.2238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8268 2.1003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6919 -0.7238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1582 2.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0939 -3.2238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7686 1.3320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3388 -1.8653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9599 1.2762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9599 -1.7238 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7521 1.1031 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8259 -0.2238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0835 1.0034 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0939 -2.2238 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0576 0.7687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8259 0.7762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0939 0.7762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9599 -0.7238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3890 0.6689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0939 -0.2238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3314 -0.0998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6628 -0.1995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9683 -0.5340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7204 0.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2278 -0.7238 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6369 -0.4342 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.6919 1.2762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8936 -1.5312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5622 -1.4314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2278 -1.7238 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 3.3573 1.0034 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 7 28 1 0 0 0 0 8 15 2 0 0 0 0 8 16 1 0 0 0 0 9 1 1 6 0 0 0 9 13 1 0 0 0 0 9 17 1 0 0 0 0 10 2 1 1 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 17 2 0 0 0 0 12 18 2 0 0 0 0 12 23 1 0 0 0 0 13 5 1 1 0 0 0 13 29 1 0 0 0 0 14 6 1 6 0 0 0 14 30 1 0 0 0 0 15 26 1 0 0 0 0 16 19 2 0 0 0 0 16 31 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 20 22 2 0 0 0 0 20 25 1 0 0 0 0 21 22 1 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 22 27 1 0 0 0 0 23 31 1 0 0 0 0 24 19 1 1 0 0 0 24 29 1 0 0 0 0 25 28 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.2
Volume:	435.096
LogP:	5.428
LogD:	3.217
LogS:	-5.055
# Rotatable Bonds:	1
TPSA:	77.38
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.618
Synthetic Accessibility Score:	5.121
Fsp3:	0.52
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.027
MDCK Permeability:	1.476225588703528e-05
Pgp-inhibitor:	0.34
Pgp-substrate:	0.945
Human Intestinal Absorption (HIA):	0.175
20% Bioavailability (F20%):	0.564
30% Bioavailability (F30%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.095
Plasma Protein Binding (PPB):	99.5360336303711%
Volume Distribution (VD):	0.755
Pgp-substrate:	1.754072904586792%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.959
CYP2C19-inhibitor:	0.111
CYP2C19-substrate:	0.944
CYP2C9-inhibitor:	0.307
CYP2C9-substrate:	0.839
CYP2D6-inhibitor:	0.088
CYP2D6-substrate:	0.15
CYP3A4-inhibitor:	0.204
CYP3A4-substrate:	0.859

ADMET: Excretion

Clearance (CL):	1.348
Half-life (T1/2):	0.117

ADMET: Toxicity

hERG Blockers:	0.053
Human Hepatotoxicity (H-HT):	0.213
Drug-inuced Liver Injury (DILI):	0.906
AMES Toxicity:	0.254
Rat Oral Acute Toxicity:	0.977
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.738
Carcinogencity:	0.098
Eye Corrosion:	0.003
Eye Irritation:	0.886
Respiratory Toxicity:	0.877

Download Data

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

Natural Product: NPC470207

Natural Product ID:	NPC470207
*Common Name:**	Dicitrinol B
IUPAC Name:	n.a.
Synonyms:	Dicitrinol B
Standard InCHIKey:	VSZGJLCADUYDAO-CBNCLHCMSA-N
Standard InCHI:	InChI=1S/C25H30O6/c1-9-13(5)29-24-19-16(8-15(26)11(3)17(9)19)31-23-12(4)18-10(2)14(6)30-25(28-7)20(18)22(27)21(23)24/h8-10,13-14,24-27H,1-7H3/t9-,10-,13-,14-,24-,25?/m1/s1
SMILES:	CC1C(OC2C3=C(C=C(C(=C13)C)O)OC4=C2C(=C5C(OC(C(C5=C4C)C)C)OC)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1822980
PubChem CID:	53466206
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
NPO33186	penicillium citrinum hgy1-5	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21761866]

☑ 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	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	6060.0	nM	PMID[570886]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	5800.0	nM	PMID[570886]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	5150.0	nM	PMID[570886]

☑ 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 NPC470207 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	426
0.1-0.2	1739
0.2-0.3	4228
0.3-0.4	11111
0.4-0.5	7588
0.5-0.6	4201
0.6-0.7	8220
0.7-0.8	4458
0.8-0.85	582
0.85-0.9	133
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC470206
0.9102	High Similarity	NPC213052
0.908	High Similarity	NPC15374
0.9057	High Similarity	NPC87708
0.9036	High Similarity	NPC259905
0.903	High Similarity	NPC178851
0.9	High Similarity	NPC114257
0.9	High Similarity	NPC299149
0.9	High Similarity	NPC153578
0.9	High Similarity	NPC277710
0.8994	High Similarity	NPC46958
0.8994	High Similarity	NPC72958
0.8994	High Similarity	NPC475246
0.8994	High Similarity	NPC232645
0.8935	High Similarity	NPC3718
0.8935	High Similarity	NPC63105
0.8931	High Similarity	NPC325983
0.8929	High Similarity	NPC271385
0.8929	High Similarity	NPC30432
0.8929	High Similarity	NPC76128
0.8929	High Similarity	NPC5029
0.8929	High Similarity	NPC111536
0.8902	High Similarity	NPC87583
0.8902	High Similarity	NPC18380
0.8896	High Similarity	NPC195167
0.8875	High Similarity	NPC325429
0.8869	High Similarity	NPC477573
0.8869	High Similarity	NPC477571
0.8869	High Similarity	NPC477572
0.8869	High Similarity	NPC298778
0.8848	High Similarity	NPC473022
0.8841	High Similarity	NPC184326
0.8841	High Similarity	NPC292863
0.8837	High Similarity	NPC475161
0.8837	High Similarity	NPC477860
0.883	High Similarity	NPC5671
0.8824	High Similarity	NPC474345
0.8824	High Similarity	NPC68381
0.882	High Similarity	NPC166067
0.8817	High Similarity	NPC91650
0.8793	High Similarity	NPC475220
0.8793	High Similarity	NPC229817
0.8793	High Similarity	NPC221140
0.8793	High Similarity	NPC473686
0.8793	High Similarity	NPC475352
0.8788	High Similarity	NPC175513
0.8788	High Similarity	NPC137232
0.8786	High Similarity	NPC475662
0.8786	High Similarity	NPC293227
0.8786	High Similarity	NPC473631
0.8786	High Similarity	NPC473717
0.8779	High Similarity	NPC84494
0.8779	High Similarity	NPC245059
0.8773	High Similarity	NPC180924
0.8772	High Similarity	NPC472661
0.8772	High Similarity	NPC475233
0.8772	High Similarity	NPC101991
0.8765	High Similarity	NPC24748
0.8765	High Similarity	NPC470335
0.8765	High Similarity	NPC59491
0.8765	High Similarity	NPC85368
0.8765	High Similarity	NPC470336
0.8758	High Similarity	NPC149526
0.8758	High Similarity	NPC474417
0.875	High Similarity	NPC97029
0.875	High Similarity	NPC158338
0.875	High Similarity	NPC65589
0.875	High Similarity	NPC97028
0.875	High Similarity	NPC100985
0.875	High Similarity	NPC288036
0.8735	High Similarity	NPC216752
0.8735	High Similarity	NPC310603
0.8728	High Similarity	NPC470453
0.8728	High Similarity	NPC164047
0.8728	High Similarity	NPC470452
0.8728	High Similarity	NPC470448
0.8727	High Similarity	NPC472618
0.8721	High Similarity	NPC246877
0.872	High Similarity	NPC164110
0.872	High Similarity	NPC212967
0.872	High Similarity	NPC246647
0.872	High Similarity	NPC96342
0.8713	High Similarity	NPC199533
0.8713	High Similarity	NPC470454
0.8704	High Similarity	NPC40356
0.8704	High Similarity	NPC154683
0.8698	High Similarity	NPC469486
0.8698	High Similarity	NPC264063
0.8698	High Similarity	NPC473202
0.8698	High Similarity	NPC222455
0.869	High Similarity	NPC477835
0.8688	High Similarity	NPC27221
0.8688	High Similarity	NPC256672
0.8688	High Similarity	NPC7025
0.8683	High Similarity	NPC290160
0.8679	High Similarity	NPC473132
0.8679	High Similarity	NPC470676
0.8679	High Similarity	NPC473135
0.8671	High Similarity	NPC121888
0.8671	High Similarity	NPC212290
0.8667	High Similarity	NPC472617
0.8667	High Similarity	NPC51760
0.8667	High Similarity	NPC186113
0.8663	High Similarity	NPC289876
0.8655	High Similarity	NPC98776
0.8655	High Similarity	NPC203751
0.8655	High Similarity	NPC131862
0.8655	High Similarity	NPC229051
0.8652	High Similarity	NPC314459
0.8652	High Similarity	NPC470199
0.865	High Similarity	NPC210942
0.865	High Similarity	NPC329844
0.865	High Similarity	NPC169990
0.8642	High Similarity	NPC478148
0.8636	High Similarity	NPC105591
0.8634	High Similarity	NPC473016
0.8631	High Similarity	NPC469664
0.8625	High Similarity	NPC22005
0.8625	High Similarity	NPC7943
0.8625	High Similarity	NPC123202
0.8623	High Similarity	NPC44947
0.8623	High Similarity	NPC190450
0.8614	High Similarity	NPC186325
0.8614	High Similarity	NPC271479
0.8614	High Similarity	NPC472320
0.8606	High Similarity	NPC272196
0.8605	High Similarity	NPC146803
0.8598	High Similarity	NPC148938
0.8589	High Similarity	NPC217447
0.8589	High Similarity	NPC5871
0.8588	High Similarity	NPC472619
0.8588	High Similarity	NPC300307
0.858	High Similarity	NPC241847
0.858	High Similarity	NPC470568
0.858	High Similarity	NPC202595
0.858	High Similarity	NPC70441
0.8571	High Similarity	NPC124155
0.8571	High Similarity	NPC35150
0.8571	High Similarity	NPC257566
0.8571	High Similarity	NPC106328
0.8571	High Similarity	NPC159508
0.8563	High Similarity	NPC47923
0.8563	High Similarity	NPC273467
0.8563	High Similarity	NPC303913
0.8563	High Similarity	NPC114652
0.8563	High Similarity	NPC189552
0.8563	High Similarity	NPC58538
0.8562	High Similarity	NPC290133
0.8562	High Similarity	NPC187282
0.8562	High Similarity	NPC24136
0.8556	High Similarity	NPC316274
0.8556	High Similarity	NPC470196
0.8556	High Similarity	NPC470193
0.8556	High Similarity	NPC282474
0.8556	High Similarity	NPC470198
0.8556	High Similarity	NPC470194
0.8556	High Similarity	NPC470195
0.8556	High Similarity	NPC470197
0.8556	High Similarity	NPC470200
0.8555	High Similarity	NPC102053
0.8554	High Similarity	NPC105584
0.8554	High Similarity	NPC474373
0.8554	High Similarity	NPC85121
0.8554	High Similarity	NPC40583
0.8554	High Similarity	NPC308265
0.8554	High Similarity	NPC177650
0.8547	High Similarity	NPC472054
0.8547	High Similarity	NPC168789
0.8545	High Similarity	NPC211482
0.8545	High Similarity	NPC476652
0.8538	High Similarity	NPC78734
0.8538	High Similarity	NPC150767
0.8537	High Similarity	NPC122365
0.8537	High Similarity	NPC213608
0.8537	High Similarity	NPC472799
0.8537	High Similarity	NPC235333
0.8537	High Similarity	NPC1477
0.8529	High Similarity	NPC472622
0.8529	High Similarity	NPC477502
0.8529	High Similarity	NPC249977
0.8529	High Similarity	NPC225419
0.8528	High Similarity	NPC78835
0.8528	High Similarity	NPC312549
0.8528	High Similarity	NPC470569
0.8528	High Similarity	NPC58668
0.8528	High Similarity	NPC204561
0.8528	High Similarity	NPC309512
0.8528	High Similarity	NPC316960
0.8528	High Similarity	NPC318424
0.8528	High Similarity	NPC106372
0.8528	High Similarity	NPC148945
0.8528	High Similarity	NPC317715
0.8528	High Similarity	NPC258249
0.8528	High Similarity	NPC209142
0.8528	High Similarity	NPC178484
0.8521	High Similarity	NPC25361
0.8521	High Similarity	NPC99216
0.8519	High Similarity	NPC329933
0.8519	High Similarity	NPC233267
0.8519	High Similarity	NPC291049

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 NPC470207 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	361
0.1-0.2	1002
0.2-0.3	1875
0.3-0.4	2742
0.4-0.5	1617
0.5-0.6	932
0.6-0.7	528
0.7-0.8	86
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9018	High Similarity	NPD6959	Discontinued
0.8655	High Similarity	NPD6559	Discontinued
0.843	Intermediate Similarity	NPD7074	Phase 3
0.8424	Intermediate Similarity	NPD7819	Suspended
0.8383	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8372	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD7054	Approved
0.8239	Intermediate Similarity	NPD8312	Approved
0.8239	Intermediate Similarity	NPD8313	Approved
0.8218	Intermediate Similarity	NPD7472	Approved
0.8204	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8198	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD7411	Suspended
0.8171	Intermediate Similarity	NPD6797	Phase 2
0.8166	Intermediate Similarity	NPD3749	Approved
0.8161	Intermediate Similarity	NPD5844	Phase 1
0.8125	Intermediate Similarity	NPD7251	Discontinued
0.8125	Intermediate Similarity	NPD1549	Phase 2
0.8079	Intermediate Similarity	NPD7808	Phase 3
0.8063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8059	Intermediate Similarity	NPD7075	Discontinued
0.8049	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7473	Discontinued
0.8024	Intermediate Similarity	NPD4380	Phase 2
0.8022	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3818	Discontinued
0.8	Intermediate Similarity	NPD7768	Phase 2
0.7989	Intermediate Similarity	NPD6166	Phase 2
0.7989	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6232	Discontinued
0.7965	Intermediate Similarity	NPD5494	Approved
0.7958	Intermediate Similarity	NPD8151	Discontinued
0.7939	Intermediate Similarity	NPD2532	Approved
0.7939	Intermediate Similarity	NPD2533	Approved
0.7939	Intermediate Similarity	NPD2534	Approved
0.7929	Intermediate Similarity	NPD1934	Approved
0.7901	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD2796	Approved
0.7879	Intermediate Similarity	NPD7390	Discontinued
0.7857	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1510	Phase 2
0.7824	Intermediate Similarity	NPD6801	Discontinued
0.7812	Intermediate Similarity	NPD1607	Approved
0.7805	Intermediate Similarity	NPD3750	Approved
0.7791	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7783	Phase 2
0.7778	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD6781	Approved
0.7725	Intermediate Similarity	NPD6777	Approved
0.7725	Intermediate Similarity	NPD6779	Approved
0.7725	Intermediate Similarity	NPD6780	Approved
0.7725	Intermediate Similarity	NPD6782	Approved
0.7725	Intermediate Similarity	NPD6778	Approved
0.7725	Intermediate Similarity	NPD6776	Approved
0.7717	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD6599	Discontinued
0.7696	Intermediate Similarity	NPD7698	Approved
0.7696	Intermediate Similarity	NPD7696	Phase 3
0.7696	Intermediate Similarity	NPD7697	Approved
0.7688	Intermediate Similarity	NPD1240	Approved
0.7674	Intermediate Similarity	NPD1465	Phase 2
0.7669	Intermediate Similarity	NPD6100	Approved
0.7669	Intermediate Similarity	NPD6099	Approved
0.7656	Intermediate Similarity	NPD7871	Phase 2
0.7656	Intermediate Similarity	NPD7870	Phase 2
0.7647	Intermediate Similarity	NPD7458	Discontinued
0.7647	Intermediate Similarity	NPD3226	Approved
0.7636	Intermediate Similarity	NPD1243	Approved
0.7636	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD920	Approved
0.7622	Intermediate Similarity	NPD2346	Discontinued
0.7619	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD7435	Discontinued
0.7598	Intermediate Similarity	NPD3751	Discontinued
0.7598	Intermediate Similarity	NPD7228	Approved
0.759	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3882	Suspended
0.7572	Intermediate Similarity	NPD2801	Approved
0.7569	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD1551	Phase 2
0.756	Intermediate Similarity	NPD1511	Approved
0.756	Intermediate Similarity	NPD6799	Approved
0.7538	Intermediate Similarity	NPD7701	Phase 2
0.753	Intermediate Similarity	NPD2800	Approved
0.7515	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD3748	Approved
0.75	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7003	Approved
0.7474	Intermediate Similarity	NPD8320	Phase 1
0.7474	Intermediate Similarity	NPD8319	Approved
0.7472	Intermediate Similarity	NPD5710	Approved
0.7472	Intermediate Similarity	NPD3787	Discontinued
0.7472	Intermediate Similarity	NPD5711	Approved
0.7471	Intermediate Similarity	NPD1512	Approved
0.7471	Intermediate Similarity	NPD8455	Phase 2
0.7461	Intermediate Similarity	NPD6823	Phase 2
0.746	Intermediate Similarity	NPD6534	Approved
0.746	Intermediate Similarity	NPD6535	Approved
0.7455	Intermediate Similarity	NPD5406	Approved
0.7455	Intermediate Similarity	NPD5408	Approved
0.7455	Intermediate Similarity	NPD5404	Approved
0.7455	Intermediate Similarity	NPD2935	Discontinued
0.7455	Intermediate Similarity	NPD5405	Approved
0.7453	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7699	Phase 2
0.7435	Intermediate Similarity	NPD7700	Phase 2
0.7429	Intermediate Similarity	NPD3817	Phase 2
0.7424	Intermediate Similarity	NPD7801	Approved
0.7416	Intermediate Similarity	NPD7199	Phase 2
0.7414	Intermediate Similarity	NPD37	Approved
0.7412	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD6234	Discontinued
0.7401	Intermediate Similarity	NPD919	Approved
0.7394	Intermediate Similarity	NPD2799	Discontinued
0.7391	Intermediate Similarity	NPD4625	Phase 3
0.7386	Intermediate Similarity	NPD4966	Approved
0.7386	Intermediate Similarity	NPD4965	Approved
0.7386	Intermediate Similarity	NPD4967	Phase 2
0.7381	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4628	Phase 3
0.7378	Intermediate Similarity	NPD6651	Approved
0.7374	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7874	Approved
0.7337	Intermediate Similarity	NPD2309	Approved
0.7333	Intermediate Similarity	NPD3926	Phase 2
0.7333	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD5402	Approved
0.7329	Intermediate Similarity	NPD4908	Phase 1
0.7326	Intermediate Similarity	NPD5403	Approved
0.7326	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD7177	Discontinued
0.7297	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5953	Discontinued
0.7278	Intermediate Similarity	NPD7229	Phase 3
0.7268	Intermediate Similarity	NPD7286	Phase 2
0.7249	Intermediate Similarity	NPD4287	Approved
0.7243	Intermediate Similarity	NPD7240	Approved
0.7239	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD8150	Discontinued
0.7225	Intermediate Similarity	NPD6212	Phase 3
0.7225	Intermediate Similarity	NPD6213	Phase 3
0.7225	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD1247	Approved
0.7222	Intermediate Similarity	NPD7584	Approved
0.7213	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5401	Approved
0.7205	Intermediate Similarity	NPD2798	Approved
0.7188	Intermediate Similarity	NPD4360	Phase 2
0.7188	Intermediate Similarity	NPD4363	Phase 3
0.7181	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD6273	Approved
0.7118	Intermediate Similarity	NPD6674	Discontinued
0.711	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD8434	Phase 2
0.7052	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD2313	Discontinued
0.7026	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4749	Approved
0.7006	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5124	Phase 1
0.7	Intermediate Similarity	NPD1471	Phase 3
0.7	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1610	Phase 2
0.6983	Remote Similarity	NPD5760	Phase 2
0.6983	Remote Similarity	NPD5761	Phase 2
0.6975	Remote Similarity	NPD1283	Approved
0.6968	Remote Similarity	NPD7685	Pre-registration
0.6966	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD943	Approved
0.6944	Remote Similarity	NPD4288	Approved
0.6933	Remote Similarity	NPD1203	Approved
0.6933	Remote Similarity	NPD1470	Approved
0.6928	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD3268	Approved
0.6909	Remote Similarity	NPD6832	Phase 2
0.6905	Remote Similarity	NPD1933	Approved
0.69	Remote Similarity	NPD7680	Approved
0.6894	Remote Similarity	NPD1201	Approved
0.6893	Remote Similarity	NPD7930	Approved
0.6893	Remote Similarity	NPD1653	Approved
0.6888	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD4361	Phase 2
0.6882	Remote Similarity	NPD4308	Phase 3
0.6882	Remote Similarity	NPD7033	Discontinued
0.6869	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6862	Remote Similarity	NPD1729	Discontinued
0.6854	Remote Similarity	NPD8059	Phase 3
0.6854	Remote Similarity	NPD8058	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