NPASS Compound

Structure

NPC270899 OpenBabel07101718332D 34 36 0 0 0 0 0 0 0 0999 V2000 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2321 -4.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -4.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7321 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2321 -4.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7321 -3.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 4 18 1 0 0 0 0 5 19 1 0 0 0 0 6 19 1 0 0 0 0 7 20 1 0 0 0 0 8 9 1 0 0 0 0 8 17 2 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 18 2 0 0 0 0 11 13 1 0 0 0 0 11 19 2 0 0 0 0 12 30 1 0 0 0 0 13 30 1 0 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 21 2 0 0 0 0 15 23 1 0 0 0 0 16 24 1 0 0 0 0 16 25 2 0 0 0 0 20 22 1 0 0 0 0 21 26 1 0 0 0 0 22 28 2 0 0 0 0 23 27 2 0 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 24 31 2 0 0 0 0 25 30 1 0 0 0 0 25 32 1 0 0 0 0 26 28 1 0 0 0 0 26 29 2 0 0 0 0 27 29 1 0 0 0 0 28 33 1 0 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.26
Volume:	510.563
LogP:	7.999
LogD:	4.596
LogS:	-4.531
# Rotatable Bonds:	6
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.354
Synthetic Accessibility Score:	3.632
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.831
MDCK Permeability:	1.3914142982685007e-05
Pgp-inhibitor:	0.038
Pgp-substrate:	0.85
Human Intestinal Absorption (HIA):	0.048
20% Bioavailability (F20%):	0.994
30% Bioavailability (F30%):	0.575

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	85.11798095703125%
Volume Distribution (VD):	1.283
Pgp-substrate:	9.842937469482422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.36
CYP1A2-substrate:	0.247
CYP2C19-inhibitor:	0.864
CYP2C19-substrate:	0.286
CYP2C9-inhibitor:	0.885
CYP2C9-substrate:	0.947
CYP2D6-inhibitor:	0.423
CYP2D6-substrate:	0.203
CYP3A4-inhibitor:	0.228
CYP3A4-substrate:	0.209

ADMET: Excretion

Clearance (CL):	15.484
Half-life (T1/2):	0.134

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.919
Drug-inuced Liver Injury (DILI):	0.553
AMES Toxicity:	0.116
Rat Oral Acute Toxicity:	0.887
Maximum Recommended Daily Dose:	0.192
Skin Sensitization:	0.182
Carcinogencity:	0.361
Eye Corrosion:	0.003
Eye Irritation:	0.746
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC270899

Natural Product ID:	NPC270899
*Common Name:**	Ferruginin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MONLTQLSGPIJEC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C30H36O4/c1-17(2)8-9-22-20(7)14-21-15-23-27(29(34)26(21)28(22)33)24(31)16-25(32)30(23,12-10-18(3)4)13-11-19(5)6/h8,10-11,14-16,32-34H,9,12-13H2,1-7H3
SMILES:	CC(=CCc1c(C)cc2cc3c(C(=O)C=C(C3(CC=C(C)C)CC=C(C)C)O)c(c2c1O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513685
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes

*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
NPO10596	Vismia sp.	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12828475]
NPO25801	Harungana madagascariensis	Species	Hypericaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[16499321]
NPO25801	Harungana madagascariensis	Species	Hypericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[17352491]
NPO25801	Harungana madagascariensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26727375]
NPO25801	Harungana madagascariensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10596	Vismia sp.	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25801	Harungana madagascariensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
GI50	3
Others	1

Activity Type	# Activity
Cell Line	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	5.0	ug.mL-1	PMID[512223]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	3.3	ug.mL-1	PMID[512223]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	4.9	ug.mL-1	PMID[512223]
NPT2	Others	Unspecified		Inhibition	=	47.0	%	PMID[512224]

☑ 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 NPC270899 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	353
0.1-0.2	1531
0.2-0.3	3184
0.3-0.4	8649
0.4-0.5	11104
0.5-0.6	5620
0.6-0.7	7364
0.7-0.8	4319
0.8-0.85	437
0.85-0.9	122
0.9-0.95	8
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9922	High Similarity	NPC249272
0.9921	High Similarity	NPC114183
0.9844	High Similarity	NPC12070
0.9769	High Similarity	NPC53001
0.9695	High Similarity	NPC87723
0.9248	High Similarity	NPC191976
0.907	High Similarity	NPC160499
0.9023	High Similarity	NPC267205
0.8955	High Similarity	NPC475088
0.8929	High Similarity	NPC12402
0.8905	High Similarity	NPC242994
0.8905	High Similarity	NPC138099
0.8897	High Similarity	NPC471905
0.8872	High Similarity	NPC17083
0.8849	High Similarity	NPC474961
0.8841	High Similarity	NPC169452
0.8841	High Similarity	NPC181560
0.8824	High Similarity	NPC118919
0.8824	High Similarity	NPC254847
0.8815	High Similarity	NPC282780
0.8815	High Similarity	NPC166480
0.8806	High Similarity	NPC58685
0.8806	High Similarity	NPC175738
0.8797	High Similarity	NPC259942
0.8788	High Similarity	NPC48248
0.8786	High Similarity	NPC163948
0.8786	High Similarity	NPC296752
0.8779	High Similarity	NPC254492
0.8777	High Similarity	NPC246638
0.8777	High Similarity	NPC110810
0.8769	High Similarity	NPC173978
0.8759	High Similarity	NPC53206
0.8759	High Similarity	NPC53414
0.875	High Similarity	NPC283088
0.875	High Similarity	NPC290803
0.8741	High Similarity	NPC37299
0.8741	High Similarity	NPC180261
0.8732	High Similarity	NPC143685
0.8723	High Similarity	NPC227841
0.8722	High Similarity	NPC92624
0.8722	High Similarity	NPC109123
0.8722	High Similarity	NPC276238
0.8714	High Similarity	NPC135524
0.8714	High Similarity	NPC193555
0.8712	High Similarity	NPC72667
0.8696	High Similarity	NPC473622
0.8676	High Similarity	NPC50924
0.8657	High Similarity	NPC55949
0.8652	High Similarity	NPC295712
0.8652	High Similarity	NPC174905
0.8652	High Similarity	NPC451542
0.8652	High Similarity	NPC293545
0.8652	High Similarity	NPC474203
0.8652	High Similarity	NPC313047
0.8647	High Similarity	NPC282923
0.8647	High Similarity	NPC96024
0.8643	High Similarity	NPC204045
0.8643	High Similarity	NPC305845
0.8636	High Similarity	NPC473691
0.8633	High Similarity	NPC143438
0.8626	High Similarity	NPC199273
0.8603	High Similarity	NPC115458
0.8603	High Similarity	NPC225051
0.8593	High Similarity	NPC474517
0.8593	High Similarity	NPC41847
0.8593	High Similarity	NPC72669
0.8582	High Similarity	NPC146647
0.8582	High Similarity	NPC34414
0.8582	High Similarity	NPC303910
0.8582	High Similarity	NPC171460
0.8571	High Similarity	NPC471530
0.8571	High Similarity	NPC116513
0.8571	High Similarity	NPC168471
0.8571	High Similarity	NPC69424
0.8571	High Similarity	NPC84672
0.8571	High Similarity	NPC176130
0.8571	High Similarity	NPC78364
0.8561	High Similarity	NPC477454
0.8551	High Similarity	NPC474311
0.8542	High Similarity	NPC37709
0.8542	High Similarity	NPC290194
0.8542	High Similarity	NPC34802
0.854	High Similarity	NPC287604
0.854	High Similarity	NPC161964
0.854	High Similarity	NPC472262
0.854	High Similarity	NPC44437
0.8531	High Similarity	NPC34482
0.8521	High Similarity	NPC471682
0.8521	High Similarity	NPC84266
0.8519	High Similarity	NPC31799
0.85	High Similarity	NPC190457
0.8496	Intermediate Similarity	NPC328983
0.8496	Intermediate Similarity	NPC3224
0.8496	Intermediate Similarity	NPC267846
0.8489	Intermediate Similarity	NPC245923
0.8489	Intermediate Similarity	NPC62272
0.8485	Intermediate Similarity	NPC142956
0.8485	Intermediate Similarity	NPC236189
0.8478	Intermediate Similarity	NPC161632
0.8472	Intermediate Similarity	NPC271944
0.8472	Intermediate Similarity	NPC110882
0.8472	Intermediate Similarity	NPC85393
0.8472	Intermediate Similarity	NPC470570
0.8467	Intermediate Similarity	NPC48036
0.8467	Intermediate Similarity	NPC314048
0.8462	Intermediate Similarity	NPC193703
0.8462	Intermediate Similarity	NPC244691
0.8462	Intermediate Similarity	NPC10764
0.8462	Intermediate Similarity	NPC471906
0.8462	Intermediate Similarity	NPC21599
0.8462	Intermediate Similarity	NPC48762
0.8456	Intermediate Similarity	NPC244699
0.8456	Intermediate Similarity	NPC205992
0.8451	Intermediate Similarity	NPC182255
0.8451	Intermediate Similarity	NPC257644
0.8451	Intermediate Similarity	NPC94076
0.8451	Intermediate Similarity	NPC19631
0.8451	Intermediate Similarity	NPC239136
0.8444	Intermediate Similarity	NPC474998
0.8444	Intermediate Similarity	NPC99731
0.8444	Intermediate Similarity	NPC278928
0.844	Intermediate Similarity	NPC315578
0.8435	Intermediate Similarity	NPC35
0.8433	Intermediate Similarity	NPC162612
0.8433	Intermediate Similarity	NPC23126
0.8433	Intermediate Similarity	NPC72158
0.8433	Intermediate Similarity	NPC316625
0.8433	Intermediate Similarity	NPC169250
0.8433	Intermediate Similarity	NPC105157
0.8433	Intermediate Similarity	NPC103356
0.8433	Intermediate Similarity	NPC100067
0.8433	Intermediate Similarity	NPC30501
0.8433	Intermediate Similarity	NPC98254
0.8433	Intermediate Similarity	NPC190043
0.8433	Intermediate Similarity	NPC329205
0.8433	Intermediate Similarity	NPC266689
0.8429	Intermediate Similarity	NPC13715
0.8429	Intermediate Similarity	NPC230811
0.8429	Intermediate Similarity	NPC4214
0.8425	Intermediate Similarity	NPC158338
0.8425	Intermediate Similarity	NPC100985
0.8425	Intermediate Similarity	NPC97028
0.8425	Intermediate Similarity	NPC288036
0.8425	Intermediate Similarity	NPC329933
0.8425	Intermediate Similarity	NPC65589
0.8425	Intermediate Similarity	NPC97029
0.8421	Intermediate Similarity	NPC103540
0.8417	Intermediate Similarity	NPC315275
0.8417	Intermediate Similarity	NPC155211
0.8417	Intermediate Similarity	NPC474813
0.8417	Intermediate Similarity	NPC272268
0.8417	Intermediate Similarity	NPC472308
0.8406	Intermediate Similarity	NPC474519
0.8403	Intermediate Similarity	NPC471683
0.8397	Intermediate Similarity	NPC154696
0.8394	Intermediate Similarity	NPC70622
0.8382	Intermediate Similarity	NPC62219
0.8382	Intermediate Similarity	NPC108129
0.8382	Intermediate Similarity	NPC17840
0.8382	Intermediate Similarity	NPC247477
0.838	Intermediate Similarity	NPC187843
0.838	Intermediate Similarity	NPC290550
0.837	Intermediate Similarity	NPC221777
0.837	Intermediate Similarity	NPC473017
0.837	Intermediate Similarity	NPC21305
0.8369	Intermediate Similarity	NPC26924
0.8369	Intermediate Similarity	NPC162939
0.8369	Intermediate Similarity	NPC472903
0.8367	Intermediate Similarity	NPC477914
0.8367	Intermediate Similarity	NPC205766
0.8358	Intermediate Similarity	NPC231774
0.8358	Intermediate Similarity	NPC62952
0.8357	Intermediate Similarity	NPC471452
0.8357	Intermediate Similarity	NPC290030
0.8357	Intermediate Similarity	NPC36868
0.8357	Intermediate Similarity	NPC305060
0.8356	Intermediate Similarity	NPC256672
0.8356	Intermediate Similarity	NPC7025
0.8356	Intermediate Similarity	NPC27221
0.8345	Intermediate Similarity	NPC80035
0.8345	Intermediate Similarity	NPC475917
0.8345	Intermediate Similarity	NPC153088
0.8333	Intermediate Similarity	NPC138472
0.8333	Intermediate Similarity	NPC176208
0.8333	Intermediate Similarity	NPC91105
0.8333	Intermediate Similarity	NPC244351
0.8333	Intermediate Similarity	NPC307174
0.8333	Intermediate Similarity	NPC53896
0.8333	Intermediate Similarity	NPC282577
0.8322	Intermediate Similarity	NPC210942
0.8322	Intermediate Similarity	NPC169990
0.8322	Intermediate Similarity	NPC73061
0.8322	Intermediate Similarity	NPC472211
0.8321	Intermediate Similarity	NPC476847
0.8321	Intermediate Similarity	NPC471851
0.8311	Intermediate Similarity	NPC478148
0.8311	Intermediate Similarity	NPC232645
0.8311	Intermediate Similarity	NPC72958
0.8311	Intermediate Similarity	NPC474417
0.8311	Intermediate Similarity	NPC149526

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 NPC270899 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	325
0.1-0.2	954
0.2-0.3	1411
0.3-0.4	2719
0.4-0.5	2231
0.5-0.6	1092
0.6-0.7	341
0.7-0.8	72
0.8-0.85	1
0.85-0.9	4
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8824	High Similarity	NPD1509	Clinical (unspecified phase)
0.8723	High Similarity	NPD7390	Discontinued
0.8538	High Similarity	NPD1201	Approved
0.8489	Intermediate Similarity	NPD5405	Approved
0.8489	Intermediate Similarity	NPD5406	Approved
0.8489	Intermediate Similarity	NPD5404	Approved
0.8489	Intermediate Similarity	NPD5408	Approved
0.8421	Intermediate Similarity	NPD1470	Approved
0.7905	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7872	Intermediate Similarity	NPD943	Approved
0.7803	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7799	Intermediate Similarity	NPD7473	Discontinued
0.7771	Intermediate Similarity	NPD6959	Discontinued
0.7761	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7819	Suspended
0.7724	Intermediate Similarity	NPD6100	Approved
0.7724	Intermediate Similarity	NPD6099	Approved
0.7722	Intermediate Similarity	NPD6232	Discontinued
0.7704	Intermediate Similarity	NPD2932	Approved
0.7671	Intermediate Similarity	NPD2346	Discontinued
0.7667	Intermediate Similarity	NPD2533	Approved
0.7667	Intermediate Similarity	NPD2534	Approved
0.7667	Intermediate Similarity	NPD2532	Approved
0.7667	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD3300	Phase 2
0.7639	Intermediate Similarity	NPD6651	Approved
0.7639	Intermediate Similarity	NPD1607	Approved
0.7626	Intermediate Similarity	NPD1164	Approved
0.7582	Intermediate Similarity	NPD3226	Approved
0.7574	Intermediate Similarity	NPD3019	Approved
0.7568	Intermediate Similarity	NPD2800	Approved
0.755	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1510	Phase 2
0.7534	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD5951	Approved
0.7517	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1240	Approved
0.75	Intermediate Similarity	NPD7635	Approved
0.75	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2935	Discontinued
0.7452	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD4750	Phase 3
0.7385	Intermediate Similarity	NPD2342	Discontinued
0.7319	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD4380	Phase 2
0.7297	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD3750	Approved
0.7285	Intermediate Similarity	NPD7003	Approved
0.7267	Intermediate Similarity	NPD1549	Phase 2
0.7255	Intermediate Similarity	NPD1511	Approved
0.725	Intermediate Similarity	NPD7075	Discontinued
0.7235	Intermediate Similarity	NPD8150	Discontinued
0.7215	Intermediate Similarity	NPD1934	Approved
0.7203	Intermediate Similarity	NPD2798	Approved
0.7197	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6599	Discontinued
0.7188	Intermediate Similarity	NPD7768	Phase 2
0.7172	Intermediate Similarity	NPD4625	Phase 3
0.717	Intermediate Similarity	NPD2801	Approved
0.717	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD1512	Approved
0.7152	Intermediate Similarity	NPD7411	Suspended
0.7143	Intermediate Similarity	NPD3023	Approved
0.7143	Intermediate Similarity	NPD3026	Approved
0.7143	Intermediate Similarity	NPD3749	Approved
0.7134	Intermediate Similarity	NPD7458	Discontinued
0.7134	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2796	Approved
0.7125	Intermediate Similarity	NPD8438	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2313	Discontinued
0.7122	Intermediate Similarity	NPD3025	Approved
0.7122	Intermediate Similarity	NPD3024	Approved
0.7097	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD2344	Approved
0.7073	Intermediate Similarity	NPD5711	Approved
0.7073	Intermediate Similarity	NPD5710	Approved
0.7071	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD9266	Approved
0.7068	Intermediate Similarity	NPD74	Approved
0.7067	Intermediate Similarity	NPD2799	Discontinued
0.7066	Intermediate Similarity	NPD6020	Phase 2
0.7066	Intermediate Similarity	NPD5844	Phase 1
0.7042	Intermediate Similarity	NPD3972	Approved
0.7029	Intermediate Similarity	NPD9493	Approved
0.702	Intermediate Similarity	NPD1551	Phase 2
0.7007	Intermediate Similarity	NPD3764	Approved
0.7	Intermediate Similarity	NPD1651	Approved
0.6993	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD9267	Approved
0.6992	Remote Similarity	NPD9263	Approved
0.6992	Remote Similarity	NPD9264	Approved
0.6975	Remote Similarity	NPD3882	Suspended
0.6971	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD6663	Approved
0.6954	Remote Similarity	NPD3748	Approved
0.6954	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD4628	Phase 3
0.6948	Remote Similarity	NPD8166	Discontinued
0.6944	Remote Similarity	NPD1283	Approved
0.6941	Remote Similarity	NPD6559	Discontinued
0.6939	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7008	Discontinued
0.6918	Remote Similarity	NPD5736	Approved
0.6903	Remote Similarity	NPD2309	Approved
0.6897	Remote Similarity	NPD1203	Approved
0.6894	Remote Similarity	NPD6801	Discontinued
0.6892	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD3268	Approved
0.6886	Remote Similarity	NPD6166	Phase 2
0.6886	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1243	Approved
0.6875	Remote Similarity	NPD1755	Approved
0.6864	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8312	Approved
0.686	Remote Similarity	NPD8313	Approved
0.6848	Remote Similarity	NPD5494	Approved
0.6842	Remote Similarity	NPD4308	Phase 3
0.6839	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7074	Phase 3
0.6815	Remote Similarity	NPD6799	Approved
0.681	Remote Similarity	NPD3817	Phase 2
0.6806	Remote Similarity	NPD4878	Approved
0.6806	Remote Similarity	NPD9269	Phase 2
0.6805	Remote Similarity	NPD7177	Discontinued
0.6798	Remote Similarity	NPD6535	Approved
0.6798	Remote Similarity	NPD6534	Approved
0.6786	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD2797	Approved
0.6779	Remote Similarity	NPD411	Approved
0.6778	Remote Similarity	NPD7699	Phase 2
0.6778	Remote Similarity	NPD7700	Phase 2
0.6765	Remote Similarity	NPD7054	Approved
0.6763	Remote Similarity	NPD9281	Approved
0.6761	Remote Similarity	NPD9268	Approved
0.6759	Remote Similarity	NPD4749	Approved
0.6757	Remote Similarity	NPD6832	Phase 2
0.6753	Remote Similarity	NPD1471	Phase 3
0.6748	Remote Similarity	NPD1465	Phase 2
0.6744	Remote Similarity	NPD844	Approved
0.6744	Remote Similarity	NPD5031	Approved
0.6744	Remote Similarity	NPD5027	Approved
0.6744	Remote Similarity	NPD1809	Phase 2
0.6744	Remote Similarity	NPD5029	Approved
0.6742	Remote Similarity	NPD6213	Phase 3
0.6742	Remote Similarity	NPD6212	Phase 3
0.6742	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD1281	Approved
0.6725	Remote Similarity	NPD7472	Approved
0.6715	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4626	Approved
0.6712	Remote Similarity	NPD6696	Suspended
0.6706	Remote Similarity	NPD3818	Discontinued
0.6705	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5028	Approved
0.6705	Remote Similarity	NPD5034	Approved
0.6705	Remote Similarity	NPD36	Approved
0.6705	Remote Similarity	NPD4955	Approved
0.6705	Remote Similarity	NPD4954	Approved
0.6705	Remote Similarity	NPD5026	Approved
0.6692	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD1930	Approved
0.6692	Remote Similarity	NPD3495	Discontinued
0.6692	Remote Similarity	NPD288	Approved
0.6692	Remote Similarity	NPD1929	Approved
0.6692	Remote Similarity	NPD9261	Approved
0.669	Remote Similarity	NPD3091	Approved
0.669	Remote Similarity	NPD1608	Approved
0.669	Remote Similarity	NPD9717	Approved
0.6667	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3094	Phase 2
0.6667	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD5038	Approved
0.6648	Remote Similarity	NPD5037	Approved
0.6647	Remote Similarity	NPD7251	Discontinued
0.6647	Remote Similarity	NPD5030	Phase 2
0.6646	Remote Similarity	NPD7236	Approved
0.6645	Remote Similarity	NPD230	Phase 1
0.6643	Remote Similarity	NPD497	Approved
0.6625	Remote Similarity	NPD6273	Approved
0.6624	Remote Similarity	NPD3400	Discontinued
0.6621	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD3092	Approved
0.662	Remote Similarity	NPD7610	Discontinued
0.6617	Remote Similarity	NPD846	Approved
0.6617	Remote Similarity	NPD940	Approved
0.6612	Remote Similarity	NPD6781	Approved
0.6612	Remote Similarity	NPD6780	Approved
0.6612	Remote Similarity	NPD6778	Approved
0.6612	Remote Similarity	NPD6776	Approved
0.6612	Remote Similarity	NPD6782	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