NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	476.28
Volume:	486.388
LogP:	2.687
LogD:	2.934
LogS:	-3.565
# Rotatable Bonds:	2
TPSA:	105.45
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	5.691
Fsp3:	0.815
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.254
MDCK Permeability:	2.100281744787935e-05
Pgp-inhibitor:	0.984
Pgp-substrate:	0.96
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.399
Plasma Protein Binding (PPB):	88.56267547607422%
Volume Distribution (VD):	1.89
Pgp-substrate:	8.206729888916016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.89
CYP2C19-inhibitor:	0.034
CYP2C19-substrate:	0.892
CYP2C9-inhibitor:	0.12
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.232
CYP3A4-inhibitor:	0.755
CYP3A4-substrate:	0.869

ADMET: Excretion

Clearance (CL):	3.431
Half-life (T1/2):	0.47

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.542
Drug-inuced Liver Injury (DILI):	0.046
AMES Toxicity:	0.685
Rat Oral Acute Toxicity:	0.978
Maximum Recommended Daily Dose:	0.958
Skin Sensitization:	0.542
Carcinogencity:	0.308
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC478051

Natural Product ID:	NPC478051
*Common Name:**	(1R,2S,4aR,4bS,7S,8aR,10aR)-3'a-hydroperoxy-2,7-dihydroxy-5'-methoxy-4b,7',8,8,10a-pentamethylspiro[2,3,4,4a,5,6,7,8a,9,10-decahydrophenanthrene-1,2'-3H-1-benzofuran]-4'-one
IUPAC Name:	(1R,2S,4aR,4bS,7S,8aR,10aR)-3'a-hydroperoxy-2,7-dihydroxy-5'-methoxy-4b,7',8,8,10a-pentamethylspiro[2,3,4,4a,5,6,7,8a,9,10-decahydrophenanthrene-1,2'-3H-1-benzofuran]-4'-one
Synonyms:	Stypohydroperoxide
Standard InCHIKey:	YSWYEMBQVGXRLL-RBVSQCECSA-N
Standard InCHI:	InChI=1S/C27H40O7/c1-15-13-16(32-6)21(30)26(34-31)14-27(33-22(15)26)20(29)8-7-18-24(4)11-10-19(28)23(2,3)17(24)9-12-25(18,27)5/h13,17-20,28-29,31H,7-12,14H2,1-6H3/t17-,18+,19-,20-,24-,25+,26?,27-/m0/s1
SMILES:	CC1=C2C(C[C@]3(O2)[C@H](CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O)C)C)O)(C(=O)C(=C1)OC)OO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44559224
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002550] Isocopalane and spongiane 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
NPO20811	Stypopodium flabelliforme	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038542]
NPO20811	Stypopodium flabelliforme	Species	Dictyotaceae	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
NPT397	Cell Line	NCI-H460	Homo sapiens	LC50	>	25000	nM	PMID[16038542]
NPT2	Others	Unspecified		LC50	>	21000	nM	PMID[16038542]

☑ 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 NPC478051 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	256
0.1-0.2	1399
0.2-0.3	4050
0.3-0.4	7066
0.4-0.5	11305
0.5-0.6	10091
0.6-0.7	6230
0.7-0.8	2111
0.8-0.85	135
0.85-0.9	52
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8718	High Similarity	NPC470777
0.8667	High Similarity	NPC24651
0.8595	High Similarity	NPC477745
0.8583	High Similarity	NPC105926
0.8583	High Similarity	NPC18945
0.8583	High Similarity	NPC91693
0.8583	High Similarity	NPC265557
0.8547	High Similarity	NPC27999
0.8547	High Similarity	NPC477116
0.8534	High Similarity	NPC247069
0.8525	High Similarity	NPC476008
0.8512	High Similarity	NPC470922
0.8512	High Similarity	NPC476729
0.85	High Similarity	NPC312833
0.8475	Intermediate Similarity	NPC297179
0.8475	Intermediate Similarity	NPC17772
0.8462	Intermediate Similarity	NPC16081
0.8462	Intermediate Similarity	NPC328374
0.8462	Intermediate Similarity	NPC173686
0.8462	Intermediate Similarity	NPC96312
0.8462	Intermediate Similarity	NPC251236
0.8462	Intermediate Similarity	NPC40632
0.8448	Intermediate Similarity	NPC198539
0.843	Intermediate Similarity	NPC67251
0.8421	Intermediate Similarity	NPC87335
0.8421	Intermediate Similarity	NPC27814
0.8417	Intermediate Similarity	NPC470779
0.839	Intermediate Similarity	NPC97908
0.839	Intermediate Similarity	NPC122033
0.839	Intermediate Similarity	NPC474654
0.839	Intermediate Similarity	NPC287343
0.839	Intermediate Similarity	NPC470854
0.8376	Intermediate Similarity	NPC268238
0.8376	Intermediate Similarity	NPC45218
0.8376	Intermediate Similarity	NPC473798
0.8376	Intermediate Similarity	NPC323821
0.8376	Intermediate Similarity	NPC143268
0.8362	Intermediate Similarity	NPC269530
0.8333	Intermediate Similarity	NPC109607
0.8333	Intermediate Similarity	NPC107338
0.8319	Intermediate Similarity	NPC251310
0.8319	Intermediate Similarity	NPC470776
0.8319	Intermediate Similarity	NPC21326
0.8305	Intermediate Similarity	NPC474734
0.8305	Intermediate Similarity	NPC207217
0.8305	Intermediate Similarity	NPC478216
0.8305	Intermediate Similarity	NPC152199
0.8305	Intermediate Similarity	NPC134869
0.8305	Intermediate Similarity	NPC235539
0.8293	Intermediate Similarity	NPC225049
0.8291	Intermediate Similarity	NPC478212
0.8291	Intermediate Similarity	NPC49451
0.8291	Intermediate Similarity	NPC477266
0.8261	Intermediate Similarity	NPC20192
0.825	Intermediate Similarity	NPC475775
0.825	Intermediate Similarity	NPC268958
0.825	Intermediate Similarity	NPC476529
0.825	Intermediate Similarity	NPC473920
0.8246	Intermediate Similarity	NPC144854
0.8246	Intermediate Similarity	NPC3316
0.8235	Intermediate Similarity	NPC470775
0.8235	Intermediate Similarity	NPC473590
0.8235	Intermediate Similarity	NPC176513
0.8235	Intermediate Similarity	NPC478204
0.822	Intermediate Similarity	NPC474906
0.822	Intermediate Similarity	NPC18547
0.8217	Intermediate Similarity	NPC596
0.8205	Intermediate Similarity	NPC90769
0.8205	Intermediate Similarity	NPC472002
0.819	Intermediate Similarity	NPC210005
0.8182	Intermediate Similarity	NPC112038
0.8174	Intermediate Similarity	NPC277017
0.8174	Intermediate Similarity	NPC154608
0.8174	Intermediate Similarity	NPC192813
0.8167	Intermediate Similarity	NPC204552
0.8167	Intermediate Similarity	NPC478206
0.8167	Intermediate Similarity	NPC478205
0.8167	Intermediate Similarity	NPC188667
0.8167	Intermediate Similarity	NPC108581
0.816	Intermediate Similarity	NPC475636
0.816	Intermediate Similarity	NPC295220
0.8158	Intermediate Similarity	NPC478052
0.8151	Intermediate Similarity	NPC474046
0.8151	Intermediate Similarity	NPC259306
0.8151	Intermediate Similarity	NPC470628
0.814	Intermediate Similarity	NPC190065
0.814	Intermediate Similarity	NPC141215
0.814	Intermediate Similarity	NPC471089
0.8136	Intermediate Similarity	NPC469454
0.8136	Intermediate Similarity	NPC469463
0.8136	Intermediate Similarity	NPC7921
0.8136	Intermediate Similarity	NPC469496
0.8136	Intermediate Similarity	NPC51978
0.8136	Intermediate Similarity	NPC208998
0.813	Intermediate Similarity	NPC227397
0.812	Intermediate Similarity	NPC471243
0.812	Intermediate Similarity	NPC476023
0.812	Intermediate Similarity	NPC201992
0.812	Intermediate Similarity	NPC171888
0.812	Intermediate Similarity	NPC97939
0.812	Intermediate Similarity	NPC100329
0.812	Intermediate Similarity	NPC247031
0.812	Intermediate Similarity	NPC132790
0.812	Intermediate Similarity	NPC188738
0.812	Intermediate Similarity	NPC146945
0.8115	Intermediate Similarity	NPC477046
0.8115	Intermediate Similarity	NPC102822
0.8103	Intermediate Similarity	NPC478210
0.8103	Intermediate Similarity	NPC141350
0.8099	Intermediate Similarity	NPC279143
0.8099	Intermediate Similarity	NPC469488
0.8099	Intermediate Similarity	NPC77689
0.8099	Intermediate Similarity	NPC473636
0.8095	Intermediate Similarity	NPC221414
0.8095	Intermediate Similarity	NPC309096
0.8095	Intermediate Similarity	NPC54614
0.8087	Intermediate Similarity	NPC473165
0.8087	Intermediate Similarity	NPC202524
0.8083	Intermediate Similarity	NPC134430
0.8083	Intermediate Similarity	NPC53396
0.8083	Intermediate Similarity	NPC98249
0.8083	Intermediate Similarity	NPC146432
0.8083	Intermediate Similarity	NPC470778
0.808	Intermediate Similarity	NPC470882
0.8077	Intermediate Similarity	NPC295885
0.8077	Intermediate Similarity	NPC140045
0.8067	Intermediate Similarity	NPC80650
0.8067	Intermediate Similarity	NPC470919
0.8067	Intermediate Similarity	NPC469877
0.8067	Intermediate Similarity	NPC326542
0.8067	Intermediate Similarity	NPC117712
0.8062	Intermediate Similarity	NPC262813
0.8051	Intermediate Similarity	NPC207251
0.8051	Intermediate Similarity	NPC474516
0.8051	Intermediate Similarity	NPC11252
0.8051	Intermediate Similarity	NPC289312
0.8047	Intermediate Similarity	NPC478151
0.8034	Intermediate Similarity	NPC478211
0.8034	Intermediate Similarity	NPC478209
0.8017	Intermediate Similarity	NPC189075
0.8017	Intermediate Similarity	NPC275539
0.8017	Intermediate Similarity	NPC284707
0.8017	Intermediate Similarity	NPC293850
0.8016	Intermediate Similarity	NPC477712
0.8016	Intermediate Similarity	NPC477713
0.8	Intermediate Similarity	NPC181357
0.8	Intermediate Similarity	NPC471332
0.8	Intermediate Similarity	NPC251998
0.8	Intermediate Similarity	NPC181999
0.8	Intermediate Similarity	NPC102352
0.8	Intermediate Similarity	NPC243014
0.8	Intermediate Similarity	NPC89929
0.8	Intermediate Similarity	NPC293112
0.8	Intermediate Similarity	NPC87662
0.8	Intermediate Similarity	NPC179626
0.8	Intermediate Similarity	NPC471333
0.7984	Intermediate Similarity	NPC120724
0.7984	Intermediate Similarity	NPC11895
0.7984	Intermediate Similarity	NPC469789
0.7983	Intermediate Similarity	NPC475966
0.7983	Intermediate Similarity	NPC317210
0.7983	Intermediate Similarity	NPC25909
0.7969	Intermediate Similarity	NPC478153
0.7969	Intermediate Similarity	NPC478154
0.7969	Intermediate Similarity	NPC478150
0.7969	Intermediate Similarity	NPC478152
0.7969	Intermediate Similarity	NPC102316
0.7969	Intermediate Similarity	NPC476193
0.7967	Intermediate Similarity	NPC275675
0.7966	Intermediate Similarity	NPC474229
0.7966	Intermediate Similarity	NPC179798
0.7966	Intermediate Similarity	NPC304180
0.7953	Intermediate Similarity	NPC231529
0.7951	Intermediate Similarity	NPC473839
0.7951	Intermediate Similarity	NPC42673
0.7951	Intermediate Similarity	NPC127530
0.7951	Intermediate Similarity	NPC230513
0.7951	Intermediate Similarity	NPC211093
0.7949	Intermediate Similarity	NPC474242
0.7937	Intermediate Similarity	NPC473265
0.7937	Intermediate Similarity	NPC473253
0.7934	Intermediate Similarity	NPC475809
0.7934	Intermediate Similarity	NPC58662
0.7934	Intermediate Similarity	NPC473968
0.7931	Intermediate Similarity	NPC230541
0.7931	Intermediate Similarity	NPC110496
0.792	Intermediate Similarity	NPC81736
0.792	Intermediate Similarity	NPC473255
0.792	Intermediate Similarity	NPC8369
0.792	Intermediate Similarity	NPC172154
0.7917	Intermediate Similarity	NPC243354
0.7917	Intermediate Similarity	NPC261330
0.7913	Intermediate Similarity	NPC474281
0.7913	Intermediate Similarity	NPC40170
0.7913	Intermediate Similarity	NPC475036
0.7903	Intermediate Similarity	NPC222688
0.7903	Intermediate Similarity	NPC170538
0.7903	Intermediate Similarity	NPC65858
0.7903	Intermediate Similarity	NPC269642
0.7899	Intermediate Similarity	NPC302146

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 NPC478051 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	1540
0.2-0.3	3672
0.3-0.4	2379
0.4-0.5	752
0.5-0.6	337
0.6-0.7	151
0.7-0.8	84
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
0.7886	Intermediate Similarity	NPD6054	Approved
0.776	Intermediate Similarity	NPD6370	Approved
0.7742	Intermediate Similarity	NPD6319	Approved
0.7742	Intermediate Similarity	NPD6059	Approved
0.7734	Intermediate Similarity	NPD7736	Approved
0.7698	Intermediate Similarity	NPD8328	Phase 3
0.768	Intermediate Similarity	NPD6015	Approved
0.768	Intermediate Similarity	NPD6016	Approved
0.7638	Intermediate Similarity	NPD7492	Approved
0.7619	Intermediate Similarity	NPD5988	Approved
0.7583	Intermediate Similarity	NPD4634	Approved
0.7578	Intermediate Similarity	NPD6616	Approved
0.7563	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD7078	Approved
0.75	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7115	Discovery
0.7459	Intermediate Similarity	NPD8297	Approved
0.7417	Intermediate Similarity	NPD6899	Approved
0.7417	Intermediate Similarity	NPD6881	Approved
0.7398	Intermediate Similarity	NPD4632	Approved
0.7395	Intermediate Similarity	NPD7128	Approved
0.7395	Intermediate Similarity	NPD5739	Approved
0.7395	Intermediate Similarity	NPD6675	Approved
0.7395	Intermediate Similarity	NPD6402	Approved
0.7385	Intermediate Similarity	NPD8293	Discontinued
0.7377	Intermediate Similarity	NPD6650	Approved
0.7377	Intermediate Similarity	NPD6649	Approved
0.7355	Intermediate Similarity	NPD6372	Approved
0.7355	Intermediate Similarity	NPD6373	Approved
0.7333	Intermediate Similarity	NPD5697	Approved
0.7295	Intermediate Similarity	NPD7290	Approved
0.7295	Intermediate Similarity	NPD6883	Approved
0.7295	Intermediate Similarity	NPD7102	Approved
0.7288	Intermediate Similarity	NPD5211	Phase 2
0.7273	Intermediate Similarity	NPD7320	Approved
0.7265	Intermediate Similarity	NPD5286	Approved
0.7265	Intermediate Similarity	NPD5285	Approved
0.7265	Intermediate Similarity	NPD4696	Approved
0.7241	Intermediate Similarity	NPD4755	Approved
0.7236	Intermediate Similarity	NPD6847	Approved
0.7236	Intermediate Similarity	NPD6869	Approved
0.7236	Intermediate Similarity	NPD8130	Phase 1
0.7236	Intermediate Similarity	NPD6617	Approved
0.7222	Intermediate Similarity	NPD6009	Approved
0.7213	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD6012	Approved
0.7213	Intermediate Similarity	NPD6013	Approved
0.7213	Intermediate Similarity	NPD6014	Approved
0.7197	Intermediate Similarity	NPD6033	Approved
0.719	Intermediate Similarity	NPD5701	Approved
0.7179	Intermediate Similarity	NPD4225	Approved
0.7177	Intermediate Similarity	NPD6882	Approved
0.7167	Intermediate Similarity	NPD5141	Approved
0.7154	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD7319	Approved
0.7143	Intermediate Similarity	NPD5225	Approved
0.7143	Intermediate Similarity	NPD5226	Approved
0.7143	Intermediate Similarity	NPD4633	Approved
0.7143	Intermediate Similarity	NPD5224	Approved
0.7132	Intermediate Similarity	NPD5983	Phase 2
0.7131	Intermediate Similarity	NPD6011	Approved
0.713	Intermediate Similarity	NPD5282	Discontinued
0.7119	Intermediate Similarity	NPD4700	Approved
0.7083	Intermediate Similarity	NPD5175	Approved
0.7083	Intermediate Similarity	NPD5174	Approved
0.7059	Intermediate Similarity	NPD5223	Approved
0.7049	Intermediate Similarity	NPD6412	Phase 2
0.7045	Intermediate Similarity	NPD6336	Discontinued
0.7045	Intermediate Similarity	NPD7507	Approved
0.7016	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4697	Phase 3
0.7009	Intermediate Similarity	NPD5222	Approved
0.7009	Intermediate Similarity	NPD5221	Approved
0.7009	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD8513	Phase 3
0.7	Intermediate Similarity	NPD8517	Approved
0.6967	Remote Similarity	NPD6008	Approved
0.696	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6079	Approved
0.6949	Remote Similarity	NPD5173	Approved
0.6949	Remote Similarity	NPD7902	Approved
0.6935	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.693	Remote Similarity	NPD5328	Approved
0.6891	Remote Similarity	NPD7638	Approved
0.6875	Remote Similarity	NPD6274	Approved
0.687	Remote Similarity	NPD7503	Approved
0.687	Remote Similarity	NPD6921	Approved
0.6855	Remote Similarity	NPD6686	Approved
0.6855	Remote Similarity	NPD4730	Approved
0.6855	Remote Similarity	NPD4729	Approved
0.6855	Remote Similarity	NPD5128	Approved
0.6846	Remote Similarity	NPD7101	Approved
0.6846	Remote Similarity	NPD7100	Approved
0.6838	Remote Similarity	NPD7748	Approved
0.6833	Remote Similarity	NPD7639	Approved
0.6833	Remote Similarity	NPD7640	Approved
0.6829	Remote Similarity	NPD4768	Approved
0.6829	Remote Similarity	NPD4767	Approved
0.6814	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3618	Phase 1
0.681	Remote Similarity	NPD7515	Phase 2
0.6807	Remote Similarity	NPD6084	Phase 2
0.6807	Remote Similarity	NPD6083	Phase 2
0.6803	Remote Similarity	NPD4754	Approved
0.6788	Remote Similarity	NPD7260	Phase 2
0.6783	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6335	Approved
0.6752	Remote Similarity	NPD5779	Approved
0.6752	Remote Similarity	NPD5778	Approved
0.6746	Remote Similarity	NPD5248	Approved
0.6746	Remote Similarity	NPD5249	Phase 3
0.6746	Remote Similarity	NPD5247	Approved
0.6746	Remote Similarity	NPD5250	Approved
0.6746	Remote Similarity	NPD5251	Approved
0.6739	Remote Similarity	NPD6845	Suspended
0.6696	Remote Similarity	NPD6110	Phase 1
0.6695	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7900	Approved
0.6693	Remote Similarity	NPD5216	Approved
0.6693	Remote Similarity	NPD5215	Approved
0.6693	Remote Similarity	NPD5217	Approved
0.6692	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD6411	Approved
0.6641	Remote Similarity	NPD6313	Approved
0.6641	Remote Similarity	NPD6053	Discontinued
0.6641	Remote Similarity	NPD6314	Approved
0.664	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD4629	Approved
0.6639	Remote Similarity	NPD5210	Approved
0.6638	Remote Similarity	NPD4753	Phase 2
0.6618	Remote Similarity	NPD8074	Phase 3
0.6617	Remote Similarity	NPD6909	Approved
0.6617	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6908	Approved
0.6615	Remote Similarity	NPD6868	Approved
0.6614	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5135	Approved
0.6614	Remote Similarity	NPD5169	Approved
0.6614	Remote Similarity	NPD6371	Approved
0.6612	Remote Similarity	NPD5696	Approved
0.661	Remote Similarity	NPD6399	Phase 3
0.661	Remote Similarity	NPD4202	Approved
0.6594	Remote Similarity	NPD5956	Approved
0.6591	Remote Similarity	NPD7516	Approved
0.6579	Remote Similarity	NPD1696	Phase 3
0.6577	Remote Similarity	NPD4695	Discontinued
0.6562	Remote Similarity	NPD5127	Approved
0.6525	Remote Similarity	NPD7983	Approved
0.6522	Remote Similarity	NPD5279	Phase 3
0.6515	Remote Similarity	NPD7328	Approved
0.6515	Remote Similarity	NPD7327	Approved
0.65	Remote Similarity	NPD5695	Phase 3
0.6496	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6101	Approved
0.6493	Remote Similarity	NPD8033	Approved
0.6491	Remote Similarity	NPD4786	Approved
0.6466	Remote Similarity	NPD7524	Approved
0.6466	Remote Similarity	NPD4522	Approved
0.6466	Remote Similarity	NPD3573	Approved
0.646	Remote Similarity	NPD3667	Approved
0.6457	Remote Similarity	NPD5168	Approved
0.6452	Remote Similarity	NPD7632	Discontinued
0.6418	Remote Similarity	NPD8294	Approved
0.6418	Remote Similarity	NPD8377	Approved
0.6412	Remote Similarity	NPD5167	Approved
0.641	Remote Similarity	NPD5737	Approved
0.641	Remote Similarity	NPD6672	Approved
0.64	Remote Similarity	NPD7236	Approved
0.6397	Remote Similarity	NPD6067	Discontinued
0.638	Remote Similarity	NPD7799	Discontinued
0.6371	Remote Similarity	NPD5344	Discontinued
0.637	Remote Similarity	NPD8378	Approved
0.637	Remote Similarity	NPD8380	Approved
0.637	Remote Similarity	NPD8335	Approved
0.637	Remote Similarity	NPD8296	Approved
0.637	Remote Similarity	NPD8379	Approved
0.6364	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD3666	Approved
0.6348	Remote Similarity	NPD3133	Approved
0.6348	Remote Similarity	NPD3665	Phase 1
0.6336	Remote Similarity	NPD8133	Approved
0.6319	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD1694	Approved
0.6293	Remote Similarity	NPD5329	Approved
0.629	Remote Similarity	NPD6648	Approved
0.6276	Remote Similarity	NPD6334	Approved
0.6276	Remote Similarity	NPD6333	Approved
0.6271	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6050	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD3617	Approved
0.625	Remote Similarity	NPD8034	Phase 2
0.6239	Remote Similarity	NPD4694	Approved
0.6239	Remote Similarity	NPD5280	Approved
0.6235	Remote Similarity	NPD8434	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data