NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	210.13
Volume:	214.173
LogP:	1.31
LogD:	1.009
LogS:	-3.057
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.616
Synthetic Accessibility Score:	5.266
Fsp3:	0.917
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.631
MDCK Permeability:	2.3600592612638138e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.264
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.041

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.965
Plasma Protein Binding (PPB):	19.88075065612793%
Volume Distribution (VD):	0.962
Pgp-substrate:	75.50852966308594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.411
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.806
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.142
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.449
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	7.963
Half-life (T1/2):	0.418

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.178
Drug-inuced Liver Injury (DILI):	0.1
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.973
Maximum Recommended Daily Dose:	0.832
Skin Sensitization:	0.694
Carcinogencity:	0.225
Eye Corrosion:	0.503
Eye Irritation:	0.509
Respiratory Toxicity:	0.951

Download Data

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

Natural Product: NPC291310

Natural Product ID:	NPC291310
*Common Name:**	Rivulalactone
IUPAC Name:	n.a.
Synonyms:	Rivulalactone
Standard InCHIKey:	INZNWRIFLOKNQB-MZQLCRGXSA-N
Standard InCHI:	InChI=1S/C12H18O3/c1-7-3-4-9(13)12-6-5-8(10(14)15-12)11(7,12)2/h7-9,13H,3-6H2,1-2H3/t7-,8+,9+,11-,12-/m0/s1
SMILES:	O=C1O[C@@]23[C@@]([C@@H]1CC2)(C)[C@@H](C)CC[C@H]3O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL505527
PubChem CID:	10656064
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000050] Lactones [CHEMONTID:0001244] Delta valerolactones

*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
NPO8475	Chiloscyphus rivularis	Species	Lophocoleaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9463110]
NPO8475	Chiloscyphus rivularis	Species	Lophocoleaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	>	500.0	ug ml-1	PMID[543804]

☑ 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 NPC291310 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	386
0.1-0.2	3182
0.2-0.3	10049
0.3-0.4	13557
0.4-0.5	6266
0.5-0.6	6640
0.6-0.7	2338
0.7-0.8	267
0.8-0.85	10
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC253995
0.8539	High Similarity	NPC470424
0.8315	Intermediate Similarity	NPC474065
0.8182	Intermediate Similarity	NPC476435
0.8172	Intermediate Similarity	NPC211087
0.8161	Intermediate Similarity	NPC80700
0.8161	Intermediate Similarity	NPC472272
0.8152	Intermediate Similarity	NPC116683
0.8148	Intermediate Similarity	NPC155441
0.8125	Intermediate Similarity	NPC100078
0.8118	Intermediate Similarity	NPC100366
0.8118	Intermediate Similarity	NPC311642
0.8118	Intermediate Similarity	NPC242771
0.8118	Intermediate Similarity	NPC164289
0.8068	Intermediate Similarity	NPC239938
0.8065	Intermediate Similarity	NPC471241
0.8041	Intermediate Similarity	NPC166079
0.8	Intermediate Similarity	NPC58631
0.8	Intermediate Similarity	NPC298266
0.8	Intermediate Similarity	NPC185529
0.8	Intermediate Similarity	NPC472146
0.8	Intermediate Similarity	NPC259654
0.7917	Intermediate Similarity	NPC244969
0.7917	Intermediate Similarity	NPC213528
0.7907	Intermediate Similarity	NPC102156
0.7907	Intermediate Similarity	NPC148740
0.7857	Intermediate Similarity	NPC306776
0.7841	Intermediate Similarity	NPC473350
0.7841	Intermediate Similarity	NPC478111
0.7835	Intermediate Similarity	NPC471253
0.7766	Intermediate Similarity	NPC476728
0.7755	Intermediate Similarity	NPC473701
0.7755	Intermediate Similarity	NPC473526
0.7742	Intermediate Similarity	NPC76136
0.7742	Intermediate Similarity	NPC329713
0.7742	Intermediate Similarity	NPC217567
0.7742	Intermediate Similarity	NPC470423
0.7738	Intermediate Similarity	NPC214030
0.7738	Intermediate Similarity	NPC83108
0.7732	Intermediate Similarity	NPC470172
0.7701	Intermediate Similarity	NPC121121
0.7692	Intermediate Similarity	NPC200580
0.7674	Intermediate Similarity	NPC477851
0.7653	Intermediate Similarity	NPC473406
0.764	Intermediate Similarity	NPC476715
0.7634	Intermediate Similarity	NPC476189
0.7614	Intermediate Similarity	NPC477285
0.7614	Intermediate Similarity	NPC259173
0.7614	Intermediate Similarity	NPC15091
0.7614	Intermediate Similarity	NPC69953
0.7614	Intermediate Similarity	NPC111582
0.7614	Intermediate Similarity	NPC227170
0.7609	Intermediate Similarity	NPC77756
0.759	Intermediate Similarity	NPC477867
0.7586	Intermediate Similarity	NPC190940
0.7582	Intermediate Similarity	NPC471221
0.7579	Intermediate Similarity	NPC475785
0.7576	Intermediate Similarity	NPC471293
0.7558	Intermediate Similarity	NPC245029
0.7558	Intermediate Similarity	NPC31302
0.7558	Intermediate Similarity	NPC80891
0.7558	Intermediate Similarity	NPC201276
0.7556	Intermediate Similarity	NPC92139
0.7556	Intermediate Similarity	NPC476727
0.7556	Intermediate Similarity	NPC476726
0.7556	Intermediate Similarity	NPC474448
0.7553	Intermediate Similarity	NPC477495
0.7551	Intermediate Similarity	NPC471254
0.7531	Intermediate Similarity	NPC98711
0.7531	Intermediate Similarity	NPC475062
0.7529	Intermediate Similarity	NPC307865
0.7528	Intermediate Similarity	NPC477434
0.7527	Intermediate Similarity	NPC52756
0.75	Intermediate Similarity	NPC24705
0.75	Intermediate Similarity	NPC286719
0.75	Intermediate Similarity	NPC317066
0.75	Intermediate Similarity	NPC477286
0.75	Intermediate Similarity	NPC97002
0.75	Intermediate Similarity	NPC56962
0.75	Intermediate Similarity	NPC61688
0.75	Intermediate Similarity	NPC212340
0.7474	Intermediate Similarity	NPC82633
0.7474	Intermediate Similarity	NPC470031
0.7474	Intermediate Similarity	NPC17336
0.7473	Intermediate Similarity	NPC470920
0.7473	Intermediate Similarity	NPC5943
0.7471	Intermediate Similarity	NPC472853
0.7471	Intermediate Similarity	NPC470609
0.7471	Intermediate Similarity	NPC134227
0.7449	Intermediate Similarity	NPC178853
0.7447	Intermediate Similarity	NPC161035
0.7447	Intermediate Similarity	NPC256104
0.7447	Intermediate Similarity	NPC472232
0.7447	Intermediate Similarity	NPC182740
0.7447	Intermediate Similarity	NPC472231
0.7447	Intermediate Similarity	NPC122083
0.7447	Intermediate Similarity	NPC211845
0.7444	Intermediate Similarity	NPC266651
0.7442	Intermediate Similarity	NPC34046
0.7442	Intermediate Similarity	NPC476732
0.7442	Intermediate Similarity	NPC224802
0.7442	Intermediate Similarity	NPC80089
0.7442	Intermediate Similarity	NPC199965
0.7442	Intermediate Similarity	NPC324700
0.7442	Intermediate Similarity	NPC171426
0.7429	Intermediate Similarity	NPC470116
0.7429	Intermediate Similarity	NPC79193
0.7429	Intermediate Similarity	NPC470115
0.7423	Intermediate Similarity	NPC472144
0.7419	Intermediate Similarity	NPC470114
0.7416	Intermediate Similarity	NPC292458
0.7416	Intermediate Similarity	NPC157328
0.7416	Intermediate Similarity	NPC29342
0.7416	Intermediate Similarity	NPC2572
0.7416	Intermediate Similarity	NPC217559
0.7416	Intermediate Similarity	NPC268578
0.74	Intermediate Similarity	NPC88469
0.7396	Intermediate Similarity	NPC475765
0.7396	Intermediate Similarity	NPC193785
0.7396	Intermediate Similarity	NPC235109
0.7396	Intermediate Similarity	NPC163685
0.7396	Intermediate Similarity	NPC256227
0.7391	Intermediate Similarity	NPC250687
0.7391	Intermediate Similarity	NPC229407
0.7391	Intermediate Similarity	NPC191221
0.7391	Intermediate Similarity	NPC48824
0.7391	Intermediate Similarity	NPC254572
0.7391	Intermediate Similarity	NPC33398
0.7386	Intermediate Similarity	NPC475743
0.7386	Intermediate Similarity	NPC12933
0.7386	Intermediate Similarity	NPC254123
0.7381	Intermediate Similarity	NPC55508
0.7381	Intermediate Similarity	NPC215030
0.7368	Intermediate Similarity	NPC206878
0.7363	Intermediate Similarity	NPC475729
0.7363	Intermediate Similarity	NPC474215
0.7363	Intermediate Similarity	NPC114378
0.7363	Intermediate Similarity	NPC215968
0.7363	Intermediate Similarity	NPC476717
0.7363	Intermediate Similarity	NPC103782
0.7363	Intermediate Similarity	NPC131365
0.7363	Intermediate Similarity	NPC155531
0.7356	Intermediate Similarity	NPC320144
0.734	Intermediate Similarity	NPC473066
0.734	Intermediate Similarity	NPC471747
0.7333	Intermediate Similarity	NPC473336
0.7333	Intermediate Similarity	NPC79308
0.7333	Intermediate Similarity	NPC471044
0.7326	Intermediate Similarity	NPC477919
0.7326	Intermediate Similarity	NPC171658
0.7326	Intermediate Similarity	NPC180199
0.7326	Intermediate Similarity	NPC143250
0.7326	Intermediate Similarity	NPC474404
0.732	Intermediate Similarity	NPC472273
0.732	Intermediate Similarity	NPC472145
0.7312	Intermediate Similarity	NPC269267
0.7303	Intermediate Similarity	NPC202688
0.7303	Intermediate Similarity	NPC477936
0.7303	Intermediate Similarity	NPC477935
0.7303	Intermediate Similarity	NPC61107
0.7303	Intermediate Similarity	NPC154043
0.7303	Intermediate Similarity	NPC289486
0.7303	Intermediate Similarity	NPC60018
0.73	Intermediate Similarity	NPC107385
0.7294	Intermediate Similarity	NPC270306
0.7294	Intermediate Similarity	NPC68565
0.7294	Intermediate Similarity	NPC159789
0.7294	Intermediate Similarity	NPC35871
0.7294	Intermediate Similarity	NPC91387
0.7294	Intermediate Similarity	NPC231680
0.7294	Intermediate Similarity	NPC212733
0.7292	Intermediate Similarity	NPC305808
0.7283	Intermediate Similarity	NPC263802
0.7273	Intermediate Similarity	NPC125366
0.7263	Intermediate Similarity	NPC472238
0.7263	Intermediate Similarity	NPC472237
0.7253	Intermediate Similarity	NPC477445
0.7241	Intermediate Similarity	NPC252483
0.7241	Intermediate Similarity	NPC191345
0.7241	Intermediate Similarity	NPC475725
0.7241	Intermediate Similarity	NPC471045
0.7241	Intermediate Similarity	NPC185465
0.7238	Intermediate Similarity	NPC477489
0.7234	Intermediate Similarity	NPC18536
0.7234	Intermediate Similarity	NPC50443
0.7228	Intermediate Similarity	NPC328737
0.7228	Intermediate Similarity	NPC470167
0.7228	Intermediate Similarity	NPC327093
0.7222	Intermediate Similarity	NPC472847
0.7209	Intermediate Similarity	NPC4209
0.7209	Intermediate Similarity	NPC472487
0.7209	Intermediate Similarity	NPC472486
0.7204	Intermediate Similarity	NPC477614
0.7204	Intermediate Similarity	NPC470009
0.7204	Intermediate Similarity	NPC56777
0.7204	Intermediate Similarity	NPC226491
0.7204	Intermediate Similarity	NPC476379
0.7204	Intermediate Similarity	NPC201607
0.7196	Intermediate Similarity	NPC49492
0.7196	Intermediate Similarity	NPC475490

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 NPC291310 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	504
0.1-0.2	3669
0.2-0.3	3321
0.3-0.4	986
0.4-0.5	345
0.5-0.6	241
0.6-0.7	78
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
0.8	Intermediate Similarity	NPD1700	Approved
0.75	Intermediate Similarity	NPD3702	Approved
0.7442	Intermediate Similarity	NPD6697	Approved
0.7442	Intermediate Similarity	NPD6118	Approved
0.7442	Intermediate Similarity	NPD6115	Approved
0.7442	Intermediate Similarity	NPD6114	Approved
0.7294	Intermediate Similarity	NPD3703	Phase 2
0.7209	Intermediate Similarity	NPD6117	Approved
0.7176	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD6116	Phase 1
0.7059	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD5777	Approved
0.6731	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3698	Phase 2
0.6706	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6628	Remote Similarity	NPD4244	Approved
0.6628	Remote Similarity	NPD4245	Approved
0.6627	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD3198	Approved
0.6542	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD7320	Approved
0.6526	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6928	Phase 2
0.6509	Remote Similarity	NPD6675	Approved
0.6509	Remote Similarity	NPD6402	Approved
0.6509	Remote Similarity	NPD7128	Approved
0.6509	Remote Similarity	NPD5739	Approved
0.6491	Remote Similarity	NPD6319	Approved
0.6484	Remote Similarity	NPD4802	Phase 2
0.6484	Remote Similarity	NPD4238	Approved
0.6481	Remote Similarity	NPD6373	Approved
0.6481	Remote Similarity	NPD6372	Approved
0.6465	Remote Similarity	NPD8034	Phase 2
0.6465	Remote Similarity	NPD8035	Phase 2
0.6455	Remote Similarity	NPD8297	Approved
0.6449	Remote Similarity	NPD5697	Approved
0.6449	Remote Similarity	NPD5701	Approved
0.641	Remote Similarity	NPD7492	Approved
0.6395	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5360	Phase 3
0.6389	Remote Similarity	NPD6881	Approved
0.6389	Remote Similarity	NPD6899	Approved
0.6389	Remote Similarity	NPD6011	Approved
0.6372	Remote Similarity	NPD6009	Approved
0.6364	Remote Similarity	NPD6650	Approved
0.6364	Remote Similarity	NPD6649	Approved
0.6356	Remote Similarity	NPD6616	Approved
0.6356	Remote Similarity	NPD7507	Approved
0.6353	Remote Similarity	NPD4224	Phase 2
0.6348	Remote Similarity	NPD6059	Approved
0.6348	Remote Similarity	NPD6054	Approved
0.633	Remote Similarity	NPD6012	Approved
0.633	Remote Similarity	NPD6014	Approved
0.633	Remote Similarity	NPD6013	Approved
0.6322	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.631	Remote Similarity	NPD371	Approved
0.6303	Remote Similarity	NPD7078	Approved
0.6303	Remote Similarity	NPD8293	Discontinued
0.6293	Remote Similarity	NPD6015	Approved
0.6293	Remote Similarity	NPD5983	Phase 2
0.6293	Remote Similarity	NPD6016	Approved
0.6277	Remote Similarity	NPD1780	Approved
0.6277	Remote Similarity	NPD1779	Approved
0.6273	Remote Similarity	NPD7102	Approved
0.6273	Remote Similarity	NPD7290	Approved
0.6273	Remote Similarity	NPD6883	Approved
0.625	Remote Similarity	NPD4789	Approved
0.625	Remote Similarity	NPD7736	Approved
0.6239	Remote Similarity	NPD6370	Approved
0.6239	Remote Similarity	NPD5988	Approved
0.6238	Remote Similarity	NPD8171	Discontinued
0.6216	Remote Similarity	NPD6869	Approved
0.6216	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD6847	Approved
0.6216	Remote Similarity	NPD6617	Approved
0.6216	Remote Similarity	NPD8130	Phase 1
0.6207	Remote Similarity	NPD229	Approved
0.6198	Remote Similarity	NPD7319	Approved
0.6186	Remote Similarity	NPD7604	Phase 2
0.6182	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.618	Remote Similarity	NPD6081	Approved
0.618	Remote Similarity	NPD4758	Discontinued
0.6161	Remote Similarity	NPD6882	Approved
0.6154	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4755	Approved
0.6129	Remote Similarity	NPD3671	Phase 1
0.6126	Remote Similarity	NPD4634	Approved
0.6118	Remote Similarity	NPD7909	Approved
0.6117	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD8133	Approved
0.61	Remote Similarity	NPD5328	Approved
0.6095	Remote Similarity	NPD7638	Approved
0.6083	Remote Similarity	NPD6336	Discontinued
0.6078	Remote Similarity	NPD6399	Phase 3
0.6078	Remote Similarity	NPD4202	Approved
0.6067	Remote Similarity	NPD4787	Phase 1
0.6038	Remote Similarity	NPD7640	Approved
0.6038	Remote Similarity	NPD4696	Approved
0.6038	Remote Similarity	NPD5285	Approved
0.6038	Remote Similarity	NPD7639	Approved
0.6038	Remote Similarity	NPD5286	Approved
0.6038	Remote Similarity	NPD8418	Phase 2
0.6038	Remote Similarity	NPD4700	Approved
0.6036	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD6001	Approved
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD6083	Phase 2
0.6	Remote Similarity	NPD6084	Phase 2
0.5984	Remote Similarity	NPD6033	Approved
0.5982	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD5223	Approved
0.598	Remote Similarity	NPD6079	Approved
0.5979	Remote Similarity	NPD3669	Approved
0.5979	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4788	Approved
0.5962	Remote Similarity	NPD5695	Phase 3
0.596	Remote Similarity	NPD3618	Phase 1
0.5948	Remote Similarity	NPD7115	Discovery
0.5948	Remote Similarity	NPD6317	Approved
0.5943	Remote Similarity	NPD5696	Approved
0.5943	Remote Similarity	NPD4225	Approved
0.5926	Remote Similarity	NPD7632	Discontinued
0.5926	Remote Similarity	NPD5211	Phase 2
0.5926	Remote Similarity	NPD5226	Approved
0.5926	Remote Similarity	NPD5224	Approved
0.5926	Remote Similarity	NPD5225	Approved
0.5926	Remote Similarity	NPD4633	Approved
0.5905	Remote Similarity	NPD4697	Phase 3
0.5897	Remote Similarity	NPD6313	Approved
0.5897	Remote Similarity	NPD6335	Approved
0.5897	Remote Similarity	NPD6314	Approved
0.5889	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6921	Approved
0.5882	Remote Similarity	NPD5207	Approved
0.5876	Remote Similarity	NPD6435	Approved
0.5872	Remote Similarity	NPD5175	Approved
0.5872	Remote Similarity	NPD4754	Approved
0.5872	Remote Similarity	NPD5174	Approved
0.5862	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6940	Discontinued
0.5856	Remote Similarity	NPD6412	Phase 2
0.5847	Remote Similarity	NPD7516	Approved
0.5847	Remote Similarity	NPD7100	Approved
0.5847	Remote Similarity	NPD7101	Approved
0.5842	Remote Similarity	NPD6903	Approved
0.5818	Remote Similarity	NPD5141	Approved
0.5812	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.58	Remote Similarity	NPD7146	Approved
0.58	Remote Similarity	NPD6684	Approved
0.58	Remote Similarity	NPD6409	Approved
0.58	Remote Similarity	NPD5330	Approved
0.58	Remote Similarity	NPD7334	Approved
0.58	Remote Similarity	NPD7521	Approved
0.5789	Remote Similarity	NPD5364	Discontinued
0.5773	Remote Similarity	NPD5369	Approved
0.5766	Remote Similarity	NPD4768	Approved
0.5766	Remote Similarity	NPD4767	Approved
0.5763	Remote Similarity	NPD7328	Approved
0.5763	Remote Similarity	NPD7327	Approved
0.5758	Remote Similarity	NPD3665	Phase 1
0.5758	Remote Similarity	NPD3133	Approved
0.5758	Remote Similarity	NPD3666	Approved
0.5758	Remote Similarity	NPD4786	Approved
0.5755	Remote Similarity	NPD5222	Approved
0.5755	Remote Similarity	NPD5221	Approved
0.5755	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.575	Remote Similarity	NPD6908	Approved
0.575	Remote Similarity	NPD6909	Approved
0.5739	Remote Similarity	NPD6053	Discontinued
0.5714	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD3667	Approved
0.5701	Remote Similarity	NPD5173	Approved
0.5686	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD5281	Approved
0.5673	Remote Similarity	NPD5284	Approved
0.567	Remote Similarity	NPD5368	Approved
0.5667	Remote Similarity	NPD8294	Approved
0.5667	Remote Similarity	NPD8377	Approved
0.5664	Remote Similarity	NPD5128	Approved
0.5664	Remote Similarity	NPD4730	Approved
0.5664	Remote Similarity	NPD4729	Approved
0.5657	Remote Similarity	NPD5362	Discontinued
0.5656	Remote Similarity	NPD6067	Discontinued
0.5644	Remote Similarity	NPD6098	Approved
0.5644	Remote Similarity	NPD5786	Approved
0.5631	Remote Similarity	NPD4753	Phase 2
0.562	Remote Similarity	NPD8380	Approved
0.562	Remote Similarity	NPD8335	Approved
0.562	Remote Similarity	NPD8033	Approved
0.562	Remote Similarity	NPD8296	Approved
0.562	Remote Similarity	NPD8379	Approved
0.562	Remote Similarity	NPD8378	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