NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	638.16
Volume:	602.115
LogP:	1.916
LogD:	0.961
LogS:	-3.567
# Rotatable Bonds:	5
TPSA:	220.26
# H-Bond Aceptor:	14
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.273
Synthetic Accessibility Score:	5.295
Fsp3:	0.438
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:	-5.966
MDCK Permeability:	6.193891294969944e-06
Pgp-inhibitor:	0.482
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.348
20% Bioavailability (F20%):	0.509
30% Bioavailability (F30%):	0.86

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	85.90056610107422%
Volume Distribution (VD):	0.586
Pgp-substrate:	6.3314080238342285%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.967
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.075
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.432
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	10.093
Half-life (T1/2):	0.015

ADMET: Toxicity

hERG Blockers:	0.032
Human Hepatotoxicity (H-HT):	0.668
Drug-inuced Liver Injury (DILI):	0.936
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.532
Maximum Recommended Daily Dose:	0.874
Skin Sensitization:	0.08
Carcinogencity:	0.114
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.49

Download Data

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

Natural Product: NPC477683

Natural Product ID:	NPC477683
*Common Name:**	rugulotrosin B
IUPAC Name:	methyl (4S,4aS)-7-[(5S,10aS)-1,5,9-trihydroxy-10a-methoxycarbonyl-3-methyl-8-oxo-6,7-dihydro-5H-xanthen-4-yl]-4,8,9-trihydroxy-6-methyl-1-oxo-3,4-dihydro-2H-xanthene-4a-carboxylate
Synonyms:
Standard InCHIKey:	ZXYUFJPVTZIRBI-WOQPHPHSSA-N
Standard InCHI:	InChI=1S/C32H30O14/c1-11-9-15(35)21-26(39)23-13(33)6-8-18(37)32(23,30(42)44-4)46-28(21)20(11)19-12(2)10-16-22(25(19)38)27(40)24-14(34)5-7-17(36)31(24,45-16)29(41)43-3/h9-10,17-18,35-40H,5-8H2,1-4H3/t17-,18-,31+,32+/m0/s1
SMILES:	CC1=CC(=C2C(=C3C(=O)CC[C@@H]([C@]3(OC2=C1C4=C(C5=C(C=C4C)O[C@@]6([C@H](CCC(=O)C6=C5O)O)C(=O)OC)O)C(=O)OC)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10461772
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds]

*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
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479323]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350167]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640527]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	Axinella verrucosa	Mediterranean	n.a.	PMID[14738391]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043411]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Sussex Inlet, New South Wales, Australia	n.a.	PMID[15104517]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332862]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Berkeley Pit lake	n.a.	PMID[17970594]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[19323568]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19326880]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20452770]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	North Sea	n.a.	PMID[21126094]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	Limonium tubiflorum	n.a.	PMID[21146414]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21916432]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22148349]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22458669]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23360521]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23477451]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23603293]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23972215]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24033077]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24437979]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31433188]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9392888]
NPO30770	Penicillium sp.	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	LD99	=	25	ug/ml	PMID[15104517]

☑ 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 NPC477683 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	389
0.1-0.2	1606
0.2-0.3	3518
0.3-0.4	8080
0.4-0.5	10161
0.5-0.6	4354
0.6-0.7	5790
0.7-0.8	7027
0.8-0.85	1553
0.85-0.9	185
0.9-0.95	26
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477682
0.9639	High Similarity	NPC86809
0.9639	High Similarity	NPC98667
0.9639	High Similarity	NPC232412
0.9581	High Similarity	NPC469345
0.9578	High Similarity	NPC154986
0.948	High Similarity	NPC48474
0.9474	High Similarity	NPC197972
0.9394	High Similarity	NPC178173
0.9341	High Similarity	NPC251144
0.9341	High Similarity	NPC241387
0.9186	High Similarity	NPC208069
0.9167	High Similarity	NPC291795
0.9167	High Similarity	NPC297195
0.9167	High Similarity	NPC207574
0.9112	High Similarity	NPC241874
0.9091	High Similarity	NPC314672
0.9053	High Similarity	NPC473096
0.9053	High Similarity	NPC473095
0.9012	High Similarity	NPC324220
0.9012	High Similarity	NPC312630
0.8994	High Similarity	NPC473094
0.8982	High Similarity	NPC473961
0.8947	High Similarity	NPC473113
0.8914	High Similarity	NPC475148
0.8914	High Similarity	NPC475656
0.8908	High Similarity	NPC84494
0.8908	High Similarity	NPC245059
0.8889	High Similarity	NPC282474
0.8889	High Similarity	NPC470200
0.8889	High Similarity	NPC470197
0.8889	High Similarity	NPC316274
0.8889	High Similarity	NPC470198
0.8889	High Similarity	NPC470193
0.8889	High Similarity	NPC470195
0.8889	High Similarity	NPC470196
0.8889	High Similarity	NPC470194
0.8882	High Similarity	NPC234497
0.8882	High Similarity	NPC470341
0.8882	High Similarity	NPC324522
0.8882	High Similarity	NPC105414
0.8882	High Similarity	NPC472058
0.8876	High Similarity	NPC472057
0.8876	High Similarity	NPC472051
0.8869	High Similarity	NPC472059
0.8857	High Similarity	NPC470452
0.8857	High Similarity	NPC477860
0.8857	High Similarity	NPC470453
0.8857	High Similarity	NPC164047
0.8857	High Similarity	NPC475161
0.8857	High Similarity	NPC470448
0.8844	High Similarity	NPC470454
0.8844	High Similarity	NPC63105
0.8844	High Similarity	NPC68381
0.8844	High Similarity	NPC294149
0.8844	High Similarity	NPC199533
0.8837	High Similarity	NPC472620
0.8817	High Similarity	NPC472053
0.8802	High Similarity	NPC186113
0.8793	High Similarity	NPC475246
0.8793	High Similarity	NPC46958
0.8786	High Similarity	NPC213052
0.8786	High Similarity	NPC470335
0.8786	High Similarity	NPC470336
0.8779	High Similarity	NPC298778
0.8779	High Similarity	NPC313304
0.8778	High Similarity	NPC470199
0.8778	High Similarity	NPC314459
0.8772	High Similarity	NPC225419
0.8772	High Similarity	NPC474024
0.8743	High Similarity	NPC246466
0.8743	High Similarity	NPC131405
0.8743	High Similarity	NPC470334
0.8736	High Similarity	NPC3718
0.8735	High Similarity	NPC237560
0.8735	High Similarity	NPC326910
0.8729	High Similarity	NPC314020
0.8728	High Similarity	NPC5029
0.8728	High Similarity	NPC271385
0.8728	High Similarity	NPC111536
0.8728	High Similarity	NPC30432
0.8728	High Similarity	NPC76128
0.8728	High Similarity	NPC477836
0.8728	High Similarity	NPC315619
0.8727	High Similarity	NPC253904
0.8727	High Similarity	NPC321363
0.8721	High Similarity	NPC326877
0.8721	High Similarity	NPC472619
0.8721	High Similarity	NPC259905
0.8721	High Similarity	NPC246274
0.8713	High Similarity	NPC178851
0.8708	High Similarity	NPC87583
0.8698	High Similarity	NPC117985
0.8693	High Similarity	NPC114257
0.8693	High Similarity	NPC299149
0.8693	High Similarity	NPC277710
0.8693	High Similarity	NPC153578
0.8686	High Similarity	NPC475233
0.8683	High Similarity	NPC472050
0.8678	High Similarity	NPC472054
0.8678	High Similarity	NPC476139
0.8678	High Similarity	NPC469393
0.8678	High Similarity	NPC229051
0.8678	High Similarity	NPC131862
0.8675	High Similarity	NPC135522
0.8671	High Similarity	NPC315306
0.8671	High Similarity	NPC193698
0.8671	High Similarity	NPC313717
0.8663	High Similarity	NPC477154
0.8663	High Similarity	NPC472622
0.8663	High Similarity	NPC63470
0.8663	High Similarity	NPC6588
0.8663	High Similarity	NPC117854
0.8663	High Similarity	NPC76647
0.8659	High Similarity	NPC174486
0.8655	High Similarity	NPC472049
0.8644	High Similarity	NPC315221
0.8639	High Similarity	NPC472055
0.8639	High Similarity	NPC470810
0.8639	High Similarity	NPC471976
0.8629	High Similarity	NPC477992
0.8629	High Similarity	NPC477991
0.8629	High Similarity	NPC474345
0.8629	High Similarity	NPC245975
0.8614	High Similarity	NPC217447
0.8614	High Similarity	NPC281272
0.8613	High Similarity	NPC54903
0.8613	High Similarity	NPC177480
0.8613	High Similarity	NPC286074
0.8613	High Similarity	NPC217378
0.8605	High Similarity	NPC20237
0.8605	High Similarity	NPC477835
0.8605	High Similarity	NPC472621
0.8603	High Similarity	NPC475352
0.8603	High Similarity	NPC221140
0.8603	High Similarity	NPC473686
0.8603	High Similarity	NPC229817
0.8603	High Similarity	NPC475220
0.8603	High Similarity	NPC241847
0.8596	High Similarity	NPC473631
0.8596	High Similarity	NPC474240
0.8596	High Similarity	NPC475662
0.8596	High Similarity	NPC293227
0.8596	High Similarity	NPC197168
0.8596	High Similarity	NPC473717
0.8596	High Similarity	NPC313452
0.8588	High Similarity	NPC3629
0.8588	High Similarity	NPC473785
0.858	High Similarity	NPC314489
0.858	High Similarity	NPC198893
0.858	High Similarity	NPC474373
0.858	High Similarity	NPC470339
0.858	High Similarity	NPC232818
0.8579	High Similarity	NPC314687
0.8571	High Similarity	NPC478027
0.8571	High Similarity	NPC146636
0.8571	High Similarity	NPC164427
0.8571	High Similarity	NPC98776
0.8571	High Similarity	NPC154341
0.8571	High Similarity	NPC476311
0.8563	High Similarity	NPC471695
0.8563	High Similarity	NPC477572
0.8563	High Similarity	NPC74559
0.8563	High Similarity	NPC477571
0.8563	High Similarity	NPC155686
0.8563	High Similarity	NPC477573
0.8556	High Similarity	NPC105591
0.8555	High Similarity	NPC469521
0.8555	High Similarity	NPC283041
0.8555	High Similarity	NPC249977
0.8554	High Similarity	NPC39819
0.8554	High Similarity	NPC232645
0.8554	High Similarity	NPC72958
0.8554	High Similarity	NPC474023
0.8554	High Similarity	NPC474021
0.8547	High Similarity	NPC469664
0.8547	High Similarity	NPC178281
0.8547	High Similarity	NPC62261
0.8547	High Similarity	NPC25361
0.8547	High Similarity	NPC475888
0.8547	High Similarity	NPC106700
0.8538	High Similarity	NPC211107
0.8538	High Similarity	NPC472402
0.8538	High Similarity	NPC473022
0.8538	High Similarity	NPC15374
0.8531	High Similarity	NPC476210
0.8531	High Similarity	NPC207467
0.8531	High Similarity	NPC476199
0.8529	High Similarity	NPC243701
0.8523	High Similarity	NPC307754
0.8523	High Similarity	NPC186800
0.8523	High Similarity	NPC19056
0.8523	High Similarity	NPC470583
0.8523	High Similarity	NPC470667
0.8523	High Similarity	NPC223735
0.8523	High Similarity	NPC162248
0.8521	High Similarity	NPC282390
0.8521	High Similarity	NPC472889
0.8521	High Similarity	NPC201127
0.8521	High Similarity	NPC44199

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 NPC477683 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	344
0.1-0.2	969
0.2-0.3	1906
0.3-0.4	2571
0.4-0.5	1861
0.5-0.6	935
0.6-0.7	392
0.7-0.8	146
0.8-0.85	24
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8659	High Similarity	NPD7879	Clinical (unspecified phase)
0.8588	High Similarity	NPD6959	Discontinued
0.8521	High Similarity	NPD7075	Discontinued
0.8506	High Similarity	NPD7804	Clinical (unspecified phase)
0.8402	Intermediate Similarity	NPD5402	Approved
0.8343	Intermediate Similarity	NPD7819	Suspended
0.8343	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6166	Phase 2
0.8333	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8324	Intermediate Similarity	NPD6232	Discontinued
0.8295	Intermediate Similarity	NPD5844	Phase 1
0.8286	Intermediate Similarity	NPD7473	Discontinued
0.8284	Intermediate Similarity	NPD6801	Discontinued
0.8268	Intermediate Similarity	NPD8313	Approved
0.8268	Intermediate Similarity	NPD8312	Approved
0.8258	Intermediate Similarity	NPD6559	Discontinued
0.8232	Intermediate Similarity	NPD8150	Discontinued
0.8212	Intermediate Similarity	NPD7808	Phase 3
0.8212	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8202	Intermediate Similarity	NPD6797	Phase 2
0.8166	Intermediate Similarity	NPD4380	Phase 2
0.8156	Intermediate Similarity	NPD7251	Discontinued
0.8142	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD3751	Discontinued
0.8129	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD7435	Discontinued
0.8095	Intermediate Similarity	NPD5403	Approved
0.8081	Intermediate Similarity	NPD3817	Phase 2
0.8059	Intermediate Similarity	NPD6599	Discontinued
0.8045	Intermediate Similarity	NPD7074	Phase 3
0.8035	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.799	Intermediate Similarity	NPD8151	Discontinued
0.7989	Intermediate Similarity	NPD7054	Approved
0.7989	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD2532	Approved
0.7976	Intermediate Similarity	NPD2534	Approved
0.7976	Intermediate Similarity	NPD2533	Approved
0.7976	Intermediate Similarity	NPD5401	Approved
0.7976	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD1934	Approved
0.7949	Intermediate Similarity	NPD7874	Approved
0.7949	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7947	Intermediate Similarity	NPD6781	Approved
0.7947	Intermediate Similarity	NPD6779	Approved
0.7947	Intermediate Similarity	NPD6782	Approved
0.7947	Intermediate Similarity	NPD6776	Approved
0.7947	Intermediate Similarity	NPD6780	Approved
0.7947	Intermediate Similarity	NPD6778	Approved
0.7947	Intermediate Similarity	NPD6777	Approved
0.7944	Intermediate Similarity	NPD7472	Approved
0.7931	Intermediate Similarity	NPD7768	Phase 2
0.7919	Intermediate Similarity	NPD1465	Phase 2
0.7917	Intermediate Similarity	NPD7696	Phase 3
0.7917	Intermediate Similarity	NPD7698	Approved
0.7917	Intermediate Similarity	NPD6799	Approved
0.7917	Intermediate Similarity	NPD7697	Approved
0.791	Intermediate Similarity	NPD3787	Discontinued
0.7908	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7908	Intermediate Similarity	NPD7783	Phase 2
0.7907	Intermediate Similarity	NPD7411	Suspended
0.7898	Intermediate Similarity	NPD5494	Approved
0.7895	Intermediate Similarity	NPD3226	Approved
0.7846	Intermediate Similarity	NPD7701	Phase 2
0.7844	Intermediate Similarity	NPD3750	Approved
0.7838	Intermediate Similarity	NPD8434	Phase 2
0.7829	Intermediate Similarity	NPD3882	Suspended
0.7816	Intermediate Similarity	NPD2801	Approved
0.7784	Intermediate Similarity	NPD3749	Approved
0.7784	Intermediate Similarity	NPD7870	Phase 2
0.7784	Intermediate Similarity	NPD8320	Phase 1
0.7784	Intermediate Similarity	NPD7871	Phase 2
0.7784	Intermediate Similarity	NPD8319	Approved
0.7771	Intermediate Similarity	NPD2346	Discontinued
0.7749	Intermediate Similarity	NPD7699	Phase 2
0.7749	Intermediate Similarity	NPD7700	Phase 2
0.7735	Intermediate Similarity	NPD3818	Discontinued
0.7735	Intermediate Similarity	NPD7228	Approved
0.7688	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6534	Approved
0.7684	Intermediate Similarity	NPD6535	Approved
0.7665	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD7801	Approved
0.7633	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD1549	Phase 2
0.7619	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD1512	Approved
0.7614	Intermediate Similarity	NPD8455	Phase 2
0.7605	Intermediate Similarity	NPD2935	Discontinued
0.7602	Intermediate Similarity	NPD7390	Discontinued
0.7594	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD6823	Phase 2
0.7561	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7557	Intermediate Similarity	NPD37	Approved
0.7545	Intermediate Similarity	NPD3748	Approved
0.7542	Intermediate Similarity	NPD6234	Discontinued
0.7529	Intermediate Similarity	NPD4628	Phase 3
0.7528	Intermediate Similarity	NPD4967	Phase 2
0.7528	Intermediate Similarity	NPD4966	Approved
0.7528	Intermediate Similarity	NPD4965	Approved
0.7514	Intermediate Similarity	NPD5711	Approved
0.7514	Intermediate Similarity	NPD5710	Approved
0.7513	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD1511	Approved
0.7444	Intermediate Similarity	NPD919	Approved
0.744	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD4060	Phase 1
0.7396	Intermediate Similarity	NPD2796	Approved
0.738	Intermediate Similarity	NPD7240	Approved
0.7368	Intermediate Similarity	NPD2800	Approved
0.7363	Intermediate Similarity	NPD1247	Approved
0.7356	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD1510	Phase 2
0.7337	Intermediate Similarity	NPD2799	Discontinued
0.7333	Intermediate Similarity	NPD4625	Phase 3
0.7326	Intermediate Similarity	NPD5953	Discontinued
0.7326	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD1607	Approved
0.7294	Intermediate Similarity	NPD6100	Approved
0.7294	Intermediate Similarity	NPD5408	Approved
0.7294	Intermediate Similarity	NPD5404	Approved
0.7294	Intermediate Similarity	NPD6099	Approved
0.7294	Intermediate Similarity	NPD5406	Approved
0.7294	Intermediate Similarity	NPD5405	Approved
0.7283	Intermediate Similarity	NPD6190	Approved
0.7283	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD3926	Phase 2
0.7273	Intermediate Similarity	NPD920	Approved
0.7267	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7259	Intermediate Similarity	NPD8285	Discontinued
0.7257	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7003	Approved
0.7202	Intermediate Similarity	NPD1240	Approved
0.7186	Intermediate Similarity	NPD2313	Discontinued
0.7186	Intermediate Similarity	NPD6798	Discontinued
0.7179	Intermediate Similarity	NPD6212	Phase 3
0.7179	Intermediate Similarity	NPD6213	Phase 3
0.7179	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD7199	Phase 2
0.7168	Intermediate Similarity	NPD1243	Approved
0.716	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5124	Phase 1
0.716	Intermediate Similarity	NPD6355	Discontinued
0.7159	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6233	Phase 2
0.7135	Intermediate Similarity	NPD7229	Phase 3
0.7129	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD7286	Phase 2
0.7119	Intermediate Similarity	NPD6273	Approved
0.7111	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD1613	Approved
0.7095	Intermediate Similarity	NPD7458	Discontinued
0.7093	Intermediate Similarity	NPD2438	Suspended
0.7083	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7985	Registered
0.7069	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7907	Approved
0.7062	Intermediate Similarity	NPD8366	Approved
0.7052	Intermediate Similarity	NPD5763	Approved
0.7052	Intermediate Similarity	NPD5762	Approved
0.705	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1653	Approved
0.7037	Intermediate Similarity	NPD8067	Phase 3
0.7029	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6651	Approved
0.7016	Intermediate Similarity	NPD7685	Pre-registration
0.701	Intermediate Similarity	NPD7584	Approved
0.7	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4288	Approved
0.6995	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD8127	Discontinued
0.6984	Remote Similarity	NPD7177	Discontinued
0.6984	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7097	Phase 1
0.6977	Remote Similarity	NPD8059	Phase 3
0.6977	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.697	Remote Similarity	NPD4360	Phase 2
0.697	Remote Similarity	NPD4363	Phase 3
0.697	Remote Similarity	NPD4749	Approved
0.6964	Remote Similarity	NPD6832	Phase 2
0.6964	Remote Similarity	NPD4908	Phase 1
0.6959	Remote Similarity	NPD447	Suspended
0.6959	Remote Similarity	NPD230	Phase 1
0.6954	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2344	Approved
0.6949	Remote Similarity	NPD3300	Phase 2

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