NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	648.29
Volume:	652.787
LogP:	4.827
LogD:	3.387
LogS:	-4.113
# Rotatable Bonds:	11
TPSA:	144.28
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.113
Synthetic Accessibility Score:	6.696
Fsp3:	0.568
Lipinski Rule-of-5:	Accepted
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:	-5.104
MDCK Permeability:	2.4643839424243197e-05
Pgp-inhibitor:	0.92
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.1
20% Bioavailability (F20%):	0.591
30% Bioavailability (F30%):	0.245

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.456
Plasma Protein Binding (PPB):	96.130859375%
Volume Distribution (VD):	2.577
Pgp-substrate:	1.7686797380447388%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.914
CYP2C19-inhibitor:	0.197
CYP2C19-substrate:	0.421
CYP2C9-inhibitor:	0.845
CYP2C9-substrate:	0.005
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.883
CYP3A4-substrate:	0.489

ADMET: Excretion

Clearance (CL):	9.791
Half-life (T1/2):	0.657

ADMET: Toxicity

hERG Blockers:	0.848
Human Hepatotoxicity (H-HT):	0.985
Drug-inuced Liver Injury (DILI):	0.911
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.689
Maximum Recommended Daily Dose:	0.989
Skin Sensitization:	0.739
Carcinogencity:	0.346
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC477188

Natural Product ID:	NPC477188
*Common Name:**	[(1R,2R,6S,7S,8R,10S,11S,12R,16R,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1Z,3Z)-nona-1,3-dienyl]-5-oxo-16-prop-1-en-2-yl-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-17-yl] benzoate
IUPAC Name:	[(1R,2R,6S,7S,8R,10S,11S,12R,16R,17R,18R)-6,7-dihydroxy-8-(hydroxymethyl)-4,18-dimethyl-14-[(1Z,3Z)-nona-1,3-dienyl]-5-oxo-16-prop-1-en-2-yl-9,13,15,19-tetraoxahexacyclo[12.4.1.01,11.02,6.08,10.012,16]nonadec-3-en-17-yl] benzoate
Synonyms:
Standard InCHIKey:	CGSGRJNIABXQJQ-SIJGATCLSA-N
Standard InCHI:	InChI=1S/C37H44O10/c1-6-7-8-9-10-11-15-18-34-45-30-26-29-33(20-38,44-29)32(41)35(42)25(19-22(4)27(35)39)37(26,47-34)23(5)28(36(30,46-34)21(2)3)43-31(40)24-16-13-12-14-17-24/h10-19,23,25-26,28-30,32,38,41-42H,2,6-9,20H2,1,3-5H3/b11-10-,18-15-/t23-,25-,26+,28-,29+,30-,32-,33+,34?,35-,36-,37+/m1/s1
SMILES:	CCCCC/C=C\C=C/C12O[C@@H]3[C@@H]4[C@H]5[C@](O5)([C@H]([C@]6([C@H]([C@@]4(O1)[C@@H]([C@H]([C@]3(O2)C(=C)C)OC(=O)C7=CC=CC=C7)C)C=C(C6=O)C)O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122180652
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

*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
NPO19476	Gnidia polycephala	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[26091146]
NPO19476	Gnidia polycephala	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19476	Gnidia polycephala	Species	Thymelaeaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT98	Individual Protein	HERG	Homo sapiens	Inhibition	=	42.5	%	PMID[26091146]

☑ 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 NPC477188 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	351
0.1-0.2	1208
0.2-0.3	2637
0.3-0.4	5280
0.4-0.5	10295
0.5-0.6	11347
0.6-0.7	9731
0.7-0.8	1461
0.8-0.85	296
0.85-0.9	54
0.9-0.95	18
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC43304
1.0	High Similarity	NPC477190
0.9804	High Similarity	NPC61891
0.98	High Similarity	NPC49297
0.9733	High Similarity	NPC181924
0.9673	High Similarity	NPC66193
0.9673	High Similarity	NPC322420
0.9608	High Similarity	NPC275477
0.9551	High Similarity	NPC40138
0.9533	High Similarity	NPC146310
0.947	High Similarity	NPC251139
0.9423	High Similarity	NPC325732
0.9423	High Similarity	NPC324769
0.9359	High Similarity	NPC471134
0.9281	High Similarity	NPC154675
0.9156	High Similarity	NPC475548
0.9156	High Similarity	NPC475638
0.9156	High Similarity	NPC290683
0.9032	High Similarity	NPC11410
0.9026	High Similarity	NPC471135
0.9007	High Similarity	NPC477737
0.8981	High Similarity	NPC323356
0.8981	High Similarity	NPC471138
0.8981	High Similarity	NPC326328
0.8981	High Similarity	NPC309991
0.8976	High Similarity	NPC254588
0.8896	High Similarity	NPC51602
0.8896	High Similarity	NPC471103
0.8854	High Similarity	NPC322048
0.8854	High Similarity	NPC318447
0.8839	High Similarity	NPC283875
0.8839	High Similarity	NPC469647
0.8839	High Similarity	NPC138641
0.8839	High Similarity	NPC22571
0.8839	High Similarity	NPC469648
0.879	High Similarity	NPC106895
0.879	High Similarity	NPC323001
0.879	High Similarity	NPC326235
0.8782	High Similarity	NPC133430
0.8782	High Similarity	NPC469477
0.8757	High Similarity	NPC186746
0.875	High Similarity	NPC478124
0.8734	High Similarity	NPC477735
0.8726	High Similarity	NPC472549
0.8726	High Similarity	NPC21410
0.8726	High Similarity	NPC473670
0.8726	High Similarity	NPC282239
0.8718	High Similarity	NPC233581
0.8718	High Similarity	NPC145649
0.871	High Similarity	NPC7095
0.8704	High Similarity	NPC477491
0.8696	High Similarity	NPC478073
0.8693	High Similarity	NPC127857
0.8679	High Similarity	NPC469399
0.8679	High Similarity	NPC477736
0.8654	High Similarity	NPC472398
0.8645	High Similarity	NPC250046
0.8645	High Similarity	NPC60509
0.8645	High Similarity	NPC81698
0.8642	High Similarity	NPC471493
0.8634	High Similarity	NPC55744
0.8616	High Similarity	NPC469417
0.8616	High Similarity	NPC472393
0.8608	High Similarity	NPC26033
0.8608	High Similarity	NPC228204
0.8599	High Similarity	NPC477905
0.8599	High Similarity	NPC472548
0.8598	High Similarity	NPC102465
0.859	High Similarity	NPC165260
0.859	High Similarity	NPC161239
0.859	High Similarity	NPC476173
0.859	High Similarity	NPC112216
0.859	High Similarity	NPC198455
0.8581	High Similarity	NPC132652
0.858	High Similarity	NPC478125
0.8571	High Similarity	NPC471100
0.8571	High Similarity	NPC471107
0.8562	High Similarity	NPC471102
0.8562	High Similarity	NPC319404
0.8553	High Similarity	NPC77493
0.8553	High Similarity	NPC217091
0.8545	High Similarity	NPC477488
0.8544	High Similarity	NPC473414
0.8544	High Similarity	NPC256142
0.8544	High Similarity	NPC229545
0.8544	High Similarity	NPC1173
0.8544	High Similarity	NPC472030
0.8544	High Similarity	NPC472022
0.8544	High Similarity	NPC248265
0.8544	High Similarity	NPC257213
0.8544	High Similarity	NPC472005
0.8544	High Similarity	NPC249471
0.8544	High Similarity	NPC158333
0.8544	High Similarity	NPC265395
0.8544	High Similarity	NPC219419
0.8544	High Similarity	NPC237549
0.8544	High Similarity	NPC11588
0.8544	High Similarity	NPC242262
0.8544	High Similarity	NPC304876
0.8544	High Similarity	NPC134685
0.8535	High Similarity	NPC470153
0.8535	High Similarity	NPC62792
0.8516	High Similarity	NPC312393
0.8516	High Similarity	NPC240115
0.8506	High Similarity	NPC471139
0.8491	Intermediate Similarity	NPC112523
0.8491	Intermediate Similarity	NPC114357
0.8491	Intermediate Similarity	NPC473611
0.8491	Intermediate Similarity	NPC132599
0.8491	Intermediate Similarity	NPC469730
0.8491	Intermediate Similarity	NPC473632
0.8491	Intermediate Similarity	NPC155329
0.8491	Intermediate Similarity	NPC114410
0.8491	Intermediate Similarity	NPC5115
0.8491	Intermediate Similarity	NPC259144
0.8471	Intermediate Similarity	NPC91730
0.8471	Intermediate Similarity	NPC470245
0.8471	Intermediate Similarity	NPC473214
0.8471	Intermediate Similarity	NPC254558
0.8466	Intermediate Similarity	NPC329960
0.8466	Intermediate Similarity	NPC150893
0.8466	Intermediate Similarity	NPC295408
0.8442	Intermediate Similarity	NPC95449
0.8442	Intermediate Similarity	NPC477894
0.8438	Intermediate Similarity	NPC70344
0.8434	Intermediate Similarity	NPC477469
0.8434	Intermediate Similarity	NPC477473
0.8434	Intermediate Similarity	NPC477466
0.8434	Intermediate Similarity	NPC477471
0.8431	Intermediate Similarity	NPC291599
0.8431	Intermediate Similarity	NPC97947
0.8431	Intermediate Similarity	NPC472576
0.8431	Intermediate Similarity	NPC87448
0.8431	Intermediate Similarity	NPC118080
0.8431	Intermediate Similarity	NPC16912
0.8431	Intermediate Similarity	NPC27377
0.8431	Intermediate Similarity	NPC41481
0.8428	Intermediate Similarity	NPC77719
0.8418	Intermediate Similarity	NPC101043
0.8418	Intermediate Similarity	NPC306799
0.8418	Intermediate Similarity	NPC197037
0.8418	Intermediate Similarity	NPC478123
0.8418	Intermediate Similarity	NPC469415
0.8418	Intermediate Similarity	NPC298072
0.8408	Intermediate Similarity	NPC473215
0.8408	Intermediate Similarity	NPC476975
0.8397	Intermediate Similarity	NPC469513
0.8393	Intermediate Similarity	NPC469421
0.8387	Intermediate Similarity	NPC34943
0.8385	Intermediate Similarity	NPC469771
0.8377	Intermediate Similarity	NPC183540
0.8377	Intermediate Similarity	NPC182869
0.8375	Intermediate Similarity	NPC469422
0.8375	Intermediate Similarity	NPC34066
0.8375	Intermediate Similarity	NPC469456
0.8373	Intermediate Similarity	NPC469420
0.8366	Intermediate Similarity	NPC97667
0.8366	Intermediate Similarity	NPC90614
0.8366	Intermediate Similarity	NPC275592
0.8366	Intermediate Similarity	NPC100913
0.8366	Intermediate Similarity	NPC171207
0.8354	Intermediate Similarity	NPC303429
0.8354	Intermediate Similarity	NPC125033
0.8354	Intermediate Similarity	NPC222102
0.8344	Intermediate Similarity	NPC327031
0.8344	Intermediate Similarity	NPC217918
0.8333	Intermediate Similarity	NPC177940
0.8333	Intermediate Similarity	NPC277053
0.8333	Intermediate Similarity	NPC174982
0.8333	Intermediate Similarity	NPC70403
0.8333	Intermediate Similarity	NPC470159
0.8333	Intermediate Similarity	NPC470157
0.8333	Intermediate Similarity	NPC200471
0.8333	Intermediate Similarity	NPC29704
0.8333	Intermediate Similarity	NPC472571
0.8333	Intermediate Similarity	NPC96903
0.8333	Intermediate Similarity	NPC469349
0.8333	Intermediate Similarity	NPC158663
0.8333	Intermediate Similarity	NPC171525
0.8333	Intermediate Similarity	NPC301946
0.8333	Intermediate Similarity	NPC476973
0.8333	Intermediate Similarity	NPC472575
0.8333	Intermediate Similarity	NPC473088
0.8333	Intermediate Similarity	NPC472572
0.8333	Intermediate Similarity	NPC184817
0.8333	Intermediate Similarity	NPC472568
0.8333	Intermediate Similarity	NPC471104
0.8313	Intermediate Similarity	NPC472658
0.8313	Intermediate Similarity	NPC472657
0.8312	Intermediate Similarity	NPC325078
0.8282	Intermediate Similarity	NPC477623
0.828	Intermediate Similarity	NPC170668
0.828	Intermediate Similarity	NPC20255
0.828	Intermediate Similarity	NPC473602
0.8269	Intermediate Similarity	NPC163719
0.8269	Intermediate Similarity	NPC125106
0.8269	Intermediate Similarity	NPC475759
0.8269	Intermediate Similarity	NPC80895
0.8269	Intermediate Similarity	NPC476974
0.8269	Intermediate Similarity	NPC472570

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 NPC477188 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	286
0.1-0.2	789
0.2-0.3	1710
0.3-0.4	3026
0.4-0.5	2210
0.5-0.6	861
0.6-0.7	240
0.7-0.8	28
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8274	Intermediate Similarity	NPD7799	Discontinued
0.8208	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD8407	Phase 2
0.8081	Intermediate Similarity	NPD8368	Discontinued
0.7974	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD7236	Approved
0.7753	Intermediate Similarity	NPD8434	Phase 2
0.7701	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD8360	Approved
0.7667	Intermediate Similarity	NPD8435	Approved
0.7667	Intermediate Similarity	NPD8361	Approved
0.7636	Intermediate Similarity	NPD7239	Suspended
0.7582	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD8150	Discontinued
0.7394	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7685	Pre-registration
0.7234	Intermediate Similarity	NPD8485	Approved
0.7225	Intermediate Similarity	NPD7057	Phase 3
0.7225	Intermediate Similarity	NPD7058	Phase 2
0.7215	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7700	Phase 2
0.7196	Intermediate Similarity	NPD7699	Phase 2
0.7184	Intermediate Similarity	NPD7075	Discontinued
0.7157	Intermediate Similarity	NPD8462	Phase 1
0.7151	Intermediate Similarity	NPD3751	Discontinued
0.715	Intermediate Similarity	NPD8319	Approved
0.715	Intermediate Similarity	NPD8320	Phase 1
0.7128	Intermediate Similarity	NPD6535	Approved
0.7128	Intermediate Similarity	NPD6534	Approved
0.7119	Intermediate Similarity	NPD3787	Discontinued
0.7111	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7819	Suspended
0.7104	Intermediate Similarity	NPD8313	Approved
0.7104	Intermediate Similarity	NPD8312	Approved
0.7098	Intermediate Similarity	NPD7435	Discontinued
0.7066	Intermediate Similarity	NPD6190	Approved
0.7056	Intermediate Similarity	NPD3818	Discontinued
0.7049	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD8389	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4965	Approved
0.7029	Intermediate Similarity	NPD4966	Approved
0.7029	Intermediate Similarity	NPD4967	Phase 2
0.7025	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD5125	Phase 3
0.7013	Intermediate Similarity	NPD5126	Approved
0.7005	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6559	Discontinued
0.6989	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.697	Remote Similarity	NPD7874	Approved
0.697	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7228	Approved
0.6957	Remote Similarity	NPD7808	Phase 3
0.6954	Remote Similarity	NPD37	Approved
0.6954	Remote Similarity	NPD6801	Discontinued
0.6949	Remote Similarity	NPD6234	Discontinued
0.6943	Remote Similarity	NPD6782	Approved
0.6943	Remote Similarity	NPD6778	Approved
0.6943	Remote Similarity	NPD6780	Approved
0.6943	Remote Similarity	NPD6776	Approved
0.6943	Remote Similarity	NPD6777	Approved
0.6943	Remote Similarity	NPD6779	Approved
0.6943	Remote Similarity	NPD6781	Approved
0.6936	Remote Similarity	NPD4380	Phase 2
0.6931	Remote Similarity	NPD8404	Phase 2
0.6923	Remote Similarity	NPD7698	Approved
0.6923	Remote Similarity	NPD7697	Approved
0.6923	Remote Similarity	NPD7696	Phase 3
0.6914	Remote Similarity	NPD5760	Phase 2
0.6914	Remote Similarity	NPD5761	Phase 2
0.691	Remote Similarity	NPD5494	Approved
0.6906	Remote Similarity	NPD7473	Discontinued
0.6902	Remote Similarity	NPD6764	Approved
0.6902	Remote Similarity	NPD7251	Discontinued
0.6902	Remote Similarity	NPD6765	Approved
0.6889	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7870	Phase 2
0.6888	Remote Similarity	NPD7871	Phase 2
0.6885	Remote Similarity	NPD7074	Phase 3
0.6875	Remote Similarity	NPD3817	Phase 2
0.6875	Remote Similarity	NPD5402	Approved
0.6872	Remote Similarity	NPD7199	Phase 2
0.6869	Remote Similarity	NPD7701	Phase 2
0.6854	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD7999	Approved
0.685	Remote Similarity	NPD7801	Approved
0.6848	Remote Similarity	NPD6797	Phase 2
0.6848	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD6599	Discontinued
0.6832	Remote Similarity	NPD7930	Approved
0.6831	Remote Similarity	NPD5844	Phase 1
0.6831	Remote Similarity	NPD7054	Approved
0.6811	Remote Similarity	NPD7240	Approved
0.681	Remote Similarity	NPD7961	Discontinued
0.6805	Remote Similarity	NPD4628	Phase 3
0.6793	Remote Similarity	NPD7472	Approved
0.6784	Remote Similarity	NPD6799	Approved
0.6768	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6166	Phase 2
0.6758	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6785	Approved
0.6755	Remote Similarity	NPD6784	Approved
0.6744	Remote Similarity	NPD2532	Approved
0.6744	Remote Similarity	NPD2534	Approved
0.6744	Remote Similarity	NPD2533	Approved
0.6742	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD3882	Suspended
0.674	Remote Similarity	NPD6232	Discontinued
0.6732	Remote Similarity	NPD2629	Approved
0.6723	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7458	Discontinued
0.6685	Remote Similarity	NPD8127	Discontinued
0.6685	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD1934	Approved
0.6667	Remote Similarity	NPD7497	Discontinued
0.6667	Remote Similarity	NPD8151	Discontinued
0.6647	Remote Similarity	NPD5401	Approved
0.6646	Remote Similarity	NPD3764	Approved
0.6635	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6212	Phase 3
0.6632	Remote Similarity	NPD6213	Phase 3
0.6632	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD8455	Phase 2
0.6627	Remote Similarity	NPD7266	Discontinued
0.6627	Remote Similarity	NPD2346	Discontinued
0.6616	Remote Similarity	NPD6823	Phase 2
0.661	Remote Similarity	NPD7411	Suspended
0.6608	Remote Similarity	NPD2575	Approved
0.6608	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD3226	Approved
0.6581	Remote Similarity	NPD4198	Discontinued
0.6561	Remote Similarity	NPD7741	Discontinued
0.6552	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7319	Approved
0.6541	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD2801	Approved
0.6529	Remote Similarity	NPD5762	Approved
0.6529	Remote Similarity	NPD5763	Approved
0.6527	Remote Similarity	NPD230	Phase 1
0.652	Remote Similarity	NPD7783	Phase 2
0.652	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD3749	Approved
0.6516	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD8166	Discontinued
0.6509	Remote Similarity	NPD2799	Discontinued
0.65	Remote Similarity	NPD7492	Approved
0.6486	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD7736	Approved
0.6478	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD7274	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD7028	Phase 2
0.646	Remote Similarity	NPD6616	Approved
0.6456	Remote Similarity	NPD6054	Approved
0.6453	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD2182	Approved
0.6429	Remote Similarity	NPD6355	Discontinued
0.6429	Remote Similarity	NPD969	Suspended
0.642	Remote Similarity	NPD7078	Approved
0.642	Remote Similarity	NPD6273	Approved
0.6415	Remote Similarity	NPD8516	Approved
0.6415	Remote Similarity	NPD8513	Phase 3
0.6415	Remote Similarity	NPD8515	Approved
0.6415	Remote Similarity	NPD8517	Approved
0.6413	Remote Similarity	NPD6959	Discontinued
0.6402	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD6085	Phase 2
0.6395	Remote Similarity	NPD1549	Phase 2
0.6395	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD919	Approved
0.6386	Remote Similarity	NPD7008	Discontinued
0.6382	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD8285	Discontinued
0.6378	Remote Similarity	NPD5711	Approved
0.6378	Remote Similarity	NPD5710	Approved
0.6375	Remote Similarity	NPD6370	Approved
0.6374	Remote Similarity	NPD2935	Discontinued
0.6374	Remote Similarity	NPD2796	Approved
0.6374	Remote Similarity	NPD7768	Phase 2
0.6364	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD7507	Approved
0.6354	Remote Similarity	NPD1465	Phase 2
0.6353	Remote Similarity	NPD7097	Phase 1
0.6347	Remote Similarity	NPD2313	Discontinued
0.6344	Remote Similarity	NPD3926	Phase 2
0.6343	Remote Similarity	NPD3300	Phase 2
0.6337	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6002	Phase 3

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