NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	516.27
Volume:	548.177
LogP:	3.928
LogD:	2.228
LogS:	-4.535
# Rotatable Bonds:	13
TPSA:	113.04
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.098
Synthetic Accessibility Score:	4.679
Fsp3:	0.552
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.752
MDCK Permeability:	2.2578888092539273e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.057
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.971
Plasma Protein Binding (PPB):	85.32682800292969%
Volume Distribution (VD):	1.167
Pgp-substrate:	15.897512435913086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.296
CYP1A2-substrate:	0.099
CYP2C19-inhibitor:	0.858
CYP2C19-substrate:	0.113
CYP2C9-inhibitor:	0.948
CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.904
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.856
CYP3A4-substrate:	0.547

ADMET: Excretion

Clearance (CL):	1.805
Half-life (T1/2):	0.873

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.856
Drug-inuced Liver Injury (DILI):	0.567
AMES Toxicity:	0.034
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.98
Carcinogencity:	0.82
Eye Corrosion:	0.016
Eye Irritation:	0.21
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC478145

Natural Product ID:	NPC478145
*Common Name:**	Vibsanin H 15,18-diacetate
IUPAC Name:	[(E)-2-[(1S,2S,7S)-5-(acetyloxymethyl)-2-[(E)-4-acetyloxy-4-methylpent-2-enyl]-2-methyl-6-oxo-7-(2-oxopropyl)cyclohept-4-en-1-yl]ethenyl] 3-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	KTRHPQOCDKSSMH-OMFZBCCCSA-N
Standard InCHI:	InChI=1S/C29H40O8/c1-19(2)16-26(33)35-15-11-25-24(17-20(3)30)27(34)23(18-36-21(4)31)10-14-29(25,8)13-9-12-28(6,7)37-22(5)32/h9-12,15-16,24-25H,13-14,17-18H2,1-8H3/b12-9+,15-11+/t24-,25-,29-/m0/s1
SMILES:	CC(=CC(=O)O/C=C/[C@H]1[C@@H](C(=O)C(=CC[C@]1(C)C/C=C/C(C)(C)OC(=O)C)COC(=O)C)CC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10436591
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12141874]
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	Eukaryota	leaves and flowers	n.a.	n.a.	PMID[14738390]
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18814	Viburnum odoratissimum	Species	Adoxaceae	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	2

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2477	Cell Line	NUGC-3	Homo sapiens	Survival	=	0	%	PMID[14738390]
NPT2	Others	Unspecified		Survival	=	0	%	PMID[14738390]

☑ 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 NPC478145 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	229
0.1-0.2	1497
0.2-0.3	5407
0.3-0.4	12481
0.4-0.5	12983
0.5-0.6	6763
0.6-0.7	2973
0.7-0.8	352
0.8-0.85	8
0.85-0.9	2
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC478144
0.8966	High Similarity	NPC145666
0.8876	High Similarity	NPC65829
0.8293	Intermediate Similarity	NPC244166
0.8046	Intermediate Similarity	NPC85772
0.8043	Intermediate Similarity	NPC284185
0.8	Intermediate Similarity	NPC128276
0.7979	Intermediate Similarity	NPC474490
0.7978	Intermediate Similarity	NPC21471
0.7978	Intermediate Similarity	NPC33570
0.7978	Intermediate Similarity	NPC261380
0.7935	Intermediate Similarity	NPC253144
0.7931	Intermediate Similarity	NPC42470
0.7931	Intermediate Similarity	NPC471325
0.7889	Intermediate Similarity	NPC38576
0.7889	Intermediate Similarity	NPC261253
0.7889	Intermediate Similarity	NPC474045
0.7889	Intermediate Similarity	NPC279859
0.7882	Intermediate Similarity	NPC57744
0.7872	Intermediate Similarity	NPC167219
0.7849	Intermediate Similarity	NPC70595
0.7849	Intermediate Similarity	NPC74103
0.7849	Intermediate Similarity	NPC150978
0.7849	Intermediate Similarity	NPC123177
0.7835	Intermediate Similarity	NPC54705
0.7812	Intermediate Similarity	NPC47834
0.7812	Intermediate Similarity	NPC53844
0.7778	Intermediate Similarity	NPC96621
0.7778	Intermediate Similarity	NPC189311
0.7753	Intermediate Similarity	NPC318468
0.7753	Intermediate Similarity	NPC475989
0.7742	Intermediate Similarity	NPC51486
0.7727	Intermediate Similarity	NPC25684
0.7727	Intermediate Similarity	NPC281949
0.7727	Intermediate Similarity	NPC301477
0.7717	Intermediate Similarity	NPC469653
0.7717	Intermediate Similarity	NPC469631
0.7717	Intermediate Similarity	NPC471047
0.7717	Intermediate Similarity	NPC469628
0.7717	Intermediate Similarity	NPC475906
0.7701	Intermediate Similarity	NPC178277
0.7701	Intermediate Similarity	NPC469690
0.7701	Intermediate Similarity	NPC469620
0.7692	Intermediate Similarity	NPC261721
0.7692	Intermediate Similarity	NPC107787
0.7684	Intermediate Similarity	NPC476415
0.7684	Intermediate Similarity	NPC470697
0.7684	Intermediate Similarity	NPC148463
0.7674	Intermediate Similarity	NPC470240
0.7674	Intermediate Similarity	NPC476794
0.7674	Intermediate Similarity	NPC65603
0.7667	Intermediate Similarity	NPC149869
0.764	Intermediate Similarity	NPC200513
0.7634	Intermediate Similarity	NPC280833
0.7634	Intermediate Similarity	NPC284561
0.7619	Intermediate Similarity	NPC470237
0.7604	Intermediate Similarity	NPC209355
0.759	Intermediate Similarity	NPC469660
0.7586	Intermediate Similarity	NPC253749
0.7586	Intermediate Similarity	NPC471220
0.7582	Intermediate Similarity	NPC161957
0.7582	Intermediate Similarity	NPC11804
0.7582	Intermediate Similarity	NPC125290
0.7582	Intermediate Similarity	NPC78089
0.7576	Intermediate Similarity	NPC206079
0.7558	Intermediate Similarity	NPC27205
0.7558	Intermediate Similarity	NPC40353
0.7556	Intermediate Similarity	NPC215294
0.7556	Intermediate Similarity	NPC53867
0.7556	Intermediate Similarity	NPC193198
0.7556	Intermediate Similarity	NPC475947
0.7553	Intermediate Similarity	NPC213636
0.7553	Intermediate Similarity	NPC253177
0.7553	Intermediate Similarity	NPC280592
0.7553	Intermediate Similarity	NPC77337
0.7551	Intermediate Similarity	NPC141191
0.7551	Intermediate Similarity	NPC54843
0.7551	Intermediate Similarity	NPC316598
0.7529	Intermediate Similarity	NPC15499
0.7529	Intermediate Similarity	NPC259599
0.7529	Intermediate Similarity	NPC294434
0.7529	Intermediate Similarity	NPC117746
0.7529	Intermediate Similarity	NPC474758
0.7528	Intermediate Similarity	NPC325031
0.7526	Intermediate Similarity	NPC9812
0.7526	Intermediate Similarity	NPC185553
0.75	Intermediate Similarity	NPC63649
0.75	Intermediate Similarity	NPC70555
0.75	Intermediate Similarity	NPC66110
0.75	Intermediate Similarity	NPC220478
0.75	Intermediate Similarity	NPC472965
0.75	Intermediate Similarity	NPC469676
0.75	Intermediate Similarity	NPC104961
0.75	Intermediate Similarity	NPC264227
0.75	Intermediate Similarity	NPC70422
0.75	Intermediate Similarity	NPC469483
0.75	Intermediate Similarity	NPC234038
0.75	Intermediate Similarity	NPC150646
0.7475	Intermediate Similarity	NPC280963
0.7474	Intermediate Similarity	NPC473944
0.7474	Intermediate Similarity	NPC261607
0.7474	Intermediate Similarity	NPC296114
0.7474	Intermediate Similarity	NPC111114
0.7474	Intermediate Similarity	NPC300312
0.7474	Intermediate Similarity	NPC221282
0.7474	Intermediate Similarity	NPC471329
0.7474	Intermediate Similarity	NPC45579
0.7474	Intermediate Similarity	NPC472705
0.7473	Intermediate Similarity	NPC475100
0.7473	Intermediate Similarity	NPC115786
0.7473	Intermediate Similarity	NPC474359
0.7471	Intermediate Similarity	NPC476325
0.7471	Intermediate Similarity	NPC476264
0.7471	Intermediate Similarity	NPC180290
0.747	Intermediate Similarity	NPC265574
0.7449	Intermediate Similarity	NPC169205
0.7449	Intermediate Similarity	NPC477949
0.7449	Intermediate Similarity	NPC2049
0.7447	Intermediate Similarity	NPC5509
0.7444	Intermediate Similarity	NPC35556
0.7444	Intermediate Similarity	NPC474291
0.7444	Intermediate Similarity	NPC471326
0.7444	Intermediate Similarity	NPC221231
0.7442	Intermediate Similarity	NPC193351
0.7442	Intermediate Similarity	NPC226669
0.7442	Intermediate Similarity	NPC138408
0.7423	Intermediate Similarity	NPC48803
0.7423	Intermediate Similarity	NPC193645
0.7423	Intermediate Similarity	NPC275960
0.7423	Intermediate Similarity	NPC90121
0.7416	Intermediate Similarity	NPC302426
0.7416	Intermediate Similarity	NPC47747
0.7404	Intermediate Similarity	NPC137911
0.7404	Intermediate Similarity	NPC47951
0.7404	Intermediate Similarity	NPC477102
0.7404	Intermediate Similarity	NPC228477
0.74	Intermediate Similarity	NPC116139
0.74	Intermediate Similarity	NPC62670
0.74	Intermediate Similarity	NPC168319
0.74	Intermediate Similarity	NPC194028
0.7396	Intermediate Similarity	NPC476416
0.7396	Intermediate Similarity	NPC248193
0.7391	Intermediate Similarity	NPC177932
0.7391	Intermediate Similarity	NPC65661
0.7391	Intermediate Similarity	NPC197903
0.7391	Intermediate Similarity	NPC99395
0.7391	Intermediate Similarity	NPC474547
0.7386	Intermediate Similarity	NPC299235
0.7379	Intermediate Similarity	NPC473911
0.7374	Intermediate Similarity	NPC244411
0.7374	Intermediate Similarity	NPC64742
0.7368	Intermediate Similarity	NPC473448
0.7368	Intermediate Similarity	NPC101651
0.7368	Intermediate Similarity	NPC471818
0.7368	Intermediate Similarity	NPC62815
0.7368	Intermediate Similarity	NPC159748
0.7368	Intermediate Similarity	NPC476437
0.7368	Intermediate Similarity	NPC476369
0.7368	Intermediate Similarity	NPC8062
0.7363	Intermediate Similarity	NPC161045
0.7363	Intermediate Similarity	NPC39588
0.7363	Intermediate Similarity	NPC475622
0.7363	Intermediate Similarity	NPC16488
0.7363	Intermediate Similarity	NPC222358
0.7363	Intermediate Similarity	NPC474703
0.7363	Intermediate Similarity	NPC108045
0.7363	Intermediate Similarity	NPC170377
0.7356	Intermediate Similarity	NPC266159
0.7356	Intermediate Similarity	NPC472967
0.7356	Intermediate Similarity	NPC474447
0.7353	Intermediate Similarity	NPC309190
0.734	Intermediate Similarity	NPC472302
0.734	Intermediate Similarity	NPC475902
0.734	Intermediate Similarity	NPC226863
0.7333	Intermediate Similarity	NPC275507
0.7333	Intermediate Similarity	NPC477103
0.7333	Intermediate Similarity	NPC282293
0.7333	Intermediate Similarity	NPC475481
0.7333	Intermediate Similarity	NPC229584
0.7333	Intermediate Similarity	NPC79277
0.7333	Intermediate Similarity	NPC141810
0.7333	Intermediate Similarity	NPC14203
0.7333	Intermediate Similarity	NPC40228
0.7327	Intermediate Similarity	NPC472754
0.7326	Intermediate Similarity	NPC140287
0.7326	Intermediate Similarity	NPC476355
0.7326	Intermediate Similarity	NPC474551
0.732	Intermediate Similarity	NPC38830
0.732	Intermediate Similarity	NPC476596
0.732	Intermediate Similarity	NPC469632
0.732	Intermediate Similarity	NPC53685
0.732	Intermediate Similarity	NPC84893
0.7312	Intermediate Similarity	NPC316426
0.7312	Intermediate Similarity	NPC315395
0.7303	Intermediate Similarity	NPC182550
0.7303	Intermediate Similarity	NPC469617
0.7303	Intermediate Similarity	NPC471299
0.7292	Intermediate Similarity	NPC219874
0.7292	Intermediate Similarity	NPC166110
0.7292	Intermediate Similarity	NPC472814

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 NPC478145 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	2011
0.2-0.3	3712
0.3-0.4	2124
0.4-0.5	762
0.5-0.6	261
0.6-0.7	51
0.7-0.8	6
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
0.764	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD5209	Approved
0.7553	Intermediate Similarity	NPD5785	Approved
0.7423	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1694	Approved
0.7241	Intermediate Similarity	NPD8039	Approved
0.717	Intermediate Similarity	NPD6371	Approved
0.7021	Intermediate Similarity	NPD5363	Approved
0.6887	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7154	Phase 3
0.6804	Remote Similarity	NPD6672	Approved
0.6804	Remote Similarity	NPD5737	Approved
0.68	Remote Similarity	NPD5282	Discontinued
0.6786	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5369	Approved
0.6771	Remote Similarity	NPD7146	Approved
0.6771	Remote Similarity	NPD5786	Approved
0.6771	Remote Similarity	NPD5330	Approved
0.6771	Remote Similarity	NPD7521	Approved
0.6771	Remote Similarity	NPD7334	Approved
0.6771	Remote Similarity	NPD6409	Approved
0.6771	Remote Similarity	NPD6684	Approved
0.6768	Remote Similarity	NPD5693	Phase 1
0.6702	Remote Similarity	NPD4269	Approved
0.6702	Remote Similarity	NPD4270	Approved
0.6701	Remote Similarity	NPD3573	Approved
0.6667	Remote Similarity	NPD6698	Approved
0.6667	Remote Similarity	NPD46	Approved
0.6637	Remote Similarity	NPD7115	Discovery
0.6634	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7900	Approved
0.6633	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6903	Approved
0.66	Remote Similarity	NPD6411	Approved
0.6566	Remote Similarity	NPD1695	Approved
0.6566	Remote Similarity	NPD6904	Approved
0.6566	Remote Similarity	NPD6673	Approved
0.6566	Remote Similarity	NPD6080	Approved
0.6538	Remote Similarity	NPD4225	Approved
0.6535	Remote Similarity	NPD5778	Approved
0.6535	Remote Similarity	NPD5779	Approved
0.6514	Remote Similarity	NPD6686	Approved
0.65	Remote Similarity	NPD7838	Discovery
0.6489	Remote Similarity	NPD4252	Approved
0.6471	Remote Similarity	NPD7748	Approved
0.6458	Remote Similarity	NPD5362	Discontinued
0.6442	Remote Similarity	NPD7902	Approved
0.6442	Remote Similarity	NPD6084	Phase 2
0.6442	Remote Similarity	NPD6083	Phase 2
0.6436	Remote Similarity	NPD7983	Approved
0.6436	Remote Similarity	NPD5694	Approved
0.6436	Remote Similarity	NPD6050	Approved
0.6408	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5695	Phase 3
0.64	Remote Similarity	NPD6101	Approved
0.64	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7638	Approved
0.6381	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6399	Phase 3
0.6354	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD6435	Approved
0.6344	Remote Similarity	NPD4756	Discovery
0.6339	Remote Similarity	NPD6650	Approved
0.6339	Remote Similarity	NPD6649	Approved
0.6337	Remote Similarity	NPD5207	Approved
0.6337	Remote Similarity	NPD5692	Phase 3
0.6327	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7640	Approved
0.6321	Remote Similarity	NPD7639	Approved
0.6316	Remote Similarity	NPD4695	Discontinued
0.63	Remote Similarity	NPD5208	Approved
0.6283	Remote Similarity	NPD6053	Discontinued
0.6279	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD7515	Phase 2
0.6263	Remote Similarity	NPD6098	Approved
0.6238	Remote Similarity	NPD6051	Approved
0.6226	Remote Similarity	NPD5696	Approved
0.6216	Remote Similarity	NPD6881	Approved
0.6216	Remote Similarity	NPD6899	Approved
0.619	Remote Similarity	NPD7839	Suspended
0.6162	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD6373	Approved
0.6161	Remote Similarity	NPD6372	Approved
0.6146	Remote Similarity	NPD5368	Approved
0.6146	Remote Similarity	NPD4821	Approved
0.6146	Remote Similarity	NPD4819	Approved
0.6146	Remote Similarity	NPD4820	Approved
0.6146	Remote Similarity	NPD4822	Approved
0.6146	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6882	Approved
0.614	Remote Similarity	NPD8297	Approved
0.6136	Remote Similarity	NPD7331	Phase 2
0.6126	Remote Similarity	NPD5697	Approved
0.6126	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD5281	Approved
0.6117	Remote Similarity	NPD5284	Approved
0.6117	Remote Similarity	NPD7637	Suspended
0.6106	Remote Similarity	NPD6883	Approved
0.6106	Remote Similarity	NPD7290	Approved
0.6106	Remote Similarity	NPD7102	Approved
0.61	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.61	Remote Similarity	NPD4519	Discontinued
0.61	Remote Similarity	NPD4623	Approved
0.6078	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD6011	Approved
0.6053	Remote Similarity	NPD6847	Approved
0.6053	Remote Similarity	NPD6869	Approved
0.6053	Remote Similarity	NPD6617	Approved
0.6053	Remote Similarity	NPD8130	Phase 1
0.604	Remote Similarity	NPD4251	Approved
0.604	Remote Similarity	NPD4250	Approved
0.6038	Remote Similarity	NPD7732	Phase 3
0.6036	Remote Similarity	NPD6402	Approved
0.6036	Remote Similarity	NPD7128	Approved
0.6036	Remote Similarity	NPD5739	Approved
0.6036	Remote Similarity	NPD6675	Approved
0.6023	Remote Similarity	NPD7341	Phase 2
0.6019	Remote Similarity	NPD6648	Approved
0.6018	Remote Similarity	NPD6012	Approved
0.6018	Remote Similarity	NPD6014	Approved
0.6018	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD6001	Approved
0.5982	Remote Similarity	NPD6614	Approved
0.5965	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD5344	Discontinued
0.5962	Remote Similarity	NPD6079	Approved
0.596	Remote Similarity	NPD5332	Approved
0.596	Remote Similarity	NPD5331	Approved
0.5943	Remote Similarity	NPD5654	Approved
0.5943	Remote Similarity	NPD5210	Approved
0.5943	Remote Similarity	NPD4629	Approved
0.5941	Remote Similarity	NPD4249	Approved
0.5941	Remote Similarity	NPD5690	Phase 2
0.5938	Remote Similarity	NPD4268	Approved
0.5938	Remote Similarity	NPD4271	Approved
0.5929	Remote Similarity	NPD7320	Approved
0.5922	Remote Similarity	NPD5370	Suspended
0.5922	Remote Similarity	NPD4753	Phase 2
0.5918	Remote Similarity	NPD4790	Discontinued
0.5917	Remote Similarity	NPD6319	Approved
0.59	Remote Similarity	NPD3666	Approved
0.59	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.59	Remote Similarity	NPD3665	Phase 1
0.59	Remote Similarity	NPD3133	Approved
0.5893	Remote Similarity	NPD6008	Approved
0.5859	Remote Similarity	NPD4223	Phase 3
0.5859	Remote Similarity	NPD4221	Approved
0.5856	Remote Similarity	NPD6052	Approved
0.5842	Remote Similarity	NPD5329	Approved
0.5841	Remote Similarity	NPD5701	Approved
0.5833	Remote Similarity	NPD5959	Approved
0.5827	Remote Similarity	NPD7260	Phase 2
0.581	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD5909	Discontinued
0.5802	Remote Similarity	NPD6927	Phase 3
0.5802	Remote Similarity	NPD28	Approved
0.5802	Remote Similarity	NPD29	Approved
0.58	Remote Similarity	NPD4788	Approved
0.5794	Remote Similarity	NPD7319	Approved
0.5789	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD3618	Phase 1
0.5784	Remote Similarity	NPD5279	Phase 3
0.5776	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5328	Approved
0.5766	Remote Similarity	NPD5211	Phase 2
0.5766	Remote Similarity	NPD7632	Discontinued
0.575	Remote Similarity	NPD6335	Approved
0.5743	Remote Similarity	NPD4786	Approved
0.5743	Remote Similarity	NPD3668	Phase 3
0.5743	Remote Similarity	NPD4197	Approved
0.5741	Remote Similarity	NPD5222	Approved
0.5741	Remote Similarity	NPD7614	Phase 1
0.5741	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5221	Approved
0.5739	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5739	Remote Similarity	NPD6413	Approved
0.5738	Remote Similarity	NPD7503	Approved
0.5727	Remote Similarity	NPD5286	Approved
0.5727	Remote Similarity	NPD5285	Approved
0.5727	Remote Similarity	NPD4696	Approved
0.5726	Remote Similarity	NPD7492	Approved
0.5714	Remote Similarity	NPD6647	Phase 2
0.5714	Remote Similarity	NPD6868	Approved
0.5702	Remote Similarity	NPD7100	Approved
0.5702	Remote Similarity	NPD7101	Approved
0.57	Remote Similarity	NPD3667	Approved
0.5699	Remote Similarity	NPD4691	Approved
0.569	Remote Similarity	NPD2067	Discontinued
0.5688	Remote Similarity	NPD5173	Approved
0.5684	Remote Similarity	NPD4058	Approved
0.568	Remote Similarity	NPD6616	Approved
0.568	Remote Similarity	NPD7507	Approved
0.5678	Remote Similarity	NPD4632	Approved
0.5676	Remote Similarity	NPD5223	Approved
0.5673	Remote Similarity	NPD4518	Approved
0.5667	Remote Similarity	NPD7500	Approved
0.5667	Remote Similarity	NPD6317	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