NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	491.041
LogP:	6.109
LogD:	5.199
LogS:	-5.797
# Rotatable Bonds:	0
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.41
Synthetic Accessibility Score:	6.207
Fsp3:	0.933
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.154
MDCK Permeability:	3.45E-05
Pgp-inhibitor:	0.414
Pgp-substrate:	0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.831
30% Bioavailability (F30%):	0.947

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	95.83%
Volume Distribution (VD):	1.179
Pgp-substrate:	2.47%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.493
CYP2C19-inhibitor:	0.089
CYP2C19-substrate:	0.946
CYP2C9-inhibitor:	0.211
CYP2C9-substrate:	0.2
CYP2D6-inhibitor:	0.167
CYP2D6-substrate:	0.614
CYP3A4-inhibitor:	0.739
CYP3A4-substrate:	0.608

ADMET: Excretion

Clearance (CL):	3.539
Half-life (T1/2):	0.17

ADMET: Toxicity

hERG Blockers:	0.376
Human Hepatotoxicity (H-HT):	0.44
Drug-inuced Liver Injury (DILI):	0.014
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.196
Maximum Recommended Daily Dose:	0.941
Skin Sensitization:	0.898
Carcinogencity:	0.018
Eye Corrosion:	0.228
Eye Irritation:	0.384
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC477578

Natural Product ID:	NPC477578
*Common Name:**	(20S)-20,28-Epoxytaraxastera-21-ene-3beta-ol
IUPAC Name:	(1R,4R,5R,8R,10S,13R,14R,17R,18S,19S,20S)-4,5,9,9,13,19,20-heptamethyl-21-oxahexacyclo[18.2.2.01,18.04,17.05,14.08,13]tetracos-23-en-10-ol
Synonyms:
Standard InCHIKey:	DNRPRCNFCIXWMI-RWENRCFFSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-19-24-20-8-9-22-26(4)12-11-23(31)25(2,3)21(26)10-13-28(22,6)27(20,5)14-16-30(24)17-15-29(19,7)32-18-30/h15,17,19-24,31H,8-14,16,18H2,1-7H3/t19-,20+,21-,22+,23-,24+,26-,27+,28+,29-,30-/m0/s1
SMILES:	C[C@H]1[C@@H]2[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC[C@]26CO[C@]1(C=C6)C)C)C)(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	16083125
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	Niigata City, Niigata Province, Japan	2000-Nov	PMID[15730243]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16933868]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17253842]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	Niigata City, Niigata Province, Japan	2001-NOV	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	stems and twigs	n.a.	n.a.	PMID[17595134]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29693393]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	Leaves; Stems	n.a.	n.a.	PMID[9214727]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10021	Nerium oleander	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10021	Nerium oleander	Species	Apocynaceae	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
IC50	5

Activity Type	# Activity
Cell Line	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1475	Cell Line	WI-38 VA13	Homo sapiens	IC50	=	111000	nM	PMID[16933868]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	316000	nM	PMID[16933868]
NPT27	Others	Unspecified		IC50	=	83800	nM	PMID[16933868]
NPT2	Others	Unspecified		IC50	=	155000	nM	PMID[16933868]

☑ 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 NPC477578 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	236
0.1-0.2	1892
0.2-0.3	5997
0.3-0.4	16408
0.4-0.5	8209
0.5-0.6	5631
0.6-0.7	3538
0.7-0.8	741
0.8-0.85	39
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9136	High Similarity	NPC304285
0.8953	High Similarity	NPC77796
0.8953	High Similarity	NPC476226
0.8953	High Similarity	NPC92885
0.878	High Similarity	NPC116202
0.8765	High Similarity	NPC291379
0.8659	High Similarity	NPC295131
0.8642	High Similarity	NPC470396
0.8642	High Similarity	NPC22955
0.8642	High Similarity	NPC474989
0.8642	High Similarity	NPC99168
0.8571	High Similarity	NPC470558
0.8537	High Similarity	NPC53744
0.8519	High Similarity	NPC34177
0.8519	High Similarity	NPC157996
0.8519	High Similarity	NPC101475
0.8519	High Similarity	NPC470750
0.8519	High Similarity	NPC40394
0.8519	High Similarity	NPC169994
0.85	High Similarity	NPC138374
0.85	High Similarity	NPC34700
0.8471	Intermediate Similarity	NPC470077
0.8415	Intermediate Similarity	NPC300499
0.8415	Intermediate Similarity	NPC196753
0.8415	Intermediate Similarity	NPC98386
0.8415	Intermediate Similarity	NPC137587
0.8415	Intermediate Similarity	NPC253807
0.8415	Intermediate Similarity	NPC230295
0.8415	Intermediate Similarity	NPC158662
0.8395	Intermediate Similarity	NPC106364
0.8395	Intermediate Similarity	NPC120098
0.8395	Intermediate Similarity	NPC265328
0.8395	Intermediate Similarity	NPC27765
0.8395	Intermediate Similarity	NPC122418
0.8395	Intermediate Similarity	NPC290598
0.8395	Intermediate Similarity	NPC30590
0.8372	Intermediate Similarity	NPC157257
0.8372	Intermediate Similarity	NPC274448
0.8293	Intermediate Similarity	NPC91594
0.8293	Intermediate Similarity	NPC470711
0.8293	Intermediate Similarity	NPC470758
0.828	Intermediate Similarity	NPC234617
0.828	Intermediate Similarity	NPC124703
0.8235	Intermediate Similarity	NPC470049
0.8235	Intermediate Similarity	NPC155521
0.8235	Intermediate Similarity	NPC471408
0.8193	Intermediate Similarity	NPC72507
0.8193	Intermediate Similarity	NPC11908
0.8182	Intermediate Similarity	NPC149224
0.8171	Intermediate Similarity	NPC470749
0.8171	Intermediate Similarity	NPC265588
0.8161	Intermediate Similarity	NPC191965
0.8148	Intermediate Similarity	NPC100334
0.8148	Intermediate Similarity	NPC477138
0.8148	Intermediate Similarity	NPC243342
0.814	Intermediate Similarity	NPC82538
0.814	Intermediate Similarity	NPC237795
0.8118	Intermediate Similarity	NPC474731
0.8118	Intermediate Similarity	NPC82986
0.8118	Intermediate Similarity	NPC7505
0.8118	Intermediate Similarity	NPC476646
0.8118	Intermediate Similarity	NPC474752
0.8118	Intermediate Similarity	NPC474683
0.8118	Intermediate Similarity	NPC474759
0.8118	Intermediate Similarity	NPC242350
0.8111	Intermediate Similarity	NPC295668
0.8105	Intermediate Similarity	NPC235142
0.8101	Intermediate Similarity	NPC210323
0.8072	Intermediate Similarity	NPC90979
0.8072	Intermediate Similarity	NPC471798
0.8072	Intermediate Similarity	NPC472805
0.8072	Intermediate Similarity	NPC470751
0.8068	Intermediate Similarity	NPC84121
0.8068	Intermediate Similarity	NPC137306
0.8049	Intermediate Similarity	NPC291503
0.8046	Intermediate Similarity	NPC238992
0.8043	Intermediate Similarity	NPC91010
0.8043	Intermediate Similarity	NPC189513
0.8025	Intermediate Similarity	NPC182717
0.8025	Intermediate Similarity	NPC471799
0.8023	Intermediate Similarity	NPC296701
0.8023	Intermediate Similarity	NPC49964
0.8023	Intermediate Similarity	NPC218616
0.8023	Intermediate Similarity	NPC47763
0.8	Intermediate Similarity	NPC474190
0.8	Intermediate Similarity	NPC96362
0.7976	Intermediate Similarity	NPC148977
0.7976	Intermediate Similarity	NPC83351
0.7976	Intermediate Similarity	NPC167891
0.7976	Intermediate Similarity	NPC476314
0.7975	Intermediate Similarity	NPC2648
0.7957	Intermediate Similarity	NPC135224
0.7957	Intermediate Similarity	NPC8774
0.7957	Intermediate Similarity	NPC477970
0.7957	Intermediate Similarity	NPC477969
0.7957	Intermediate Similarity	NPC100892
0.7955	Intermediate Similarity	NPC266511
0.7952	Intermediate Similarity	NPC106432
0.7935	Intermediate Similarity	NPC27531
0.7931	Intermediate Similarity	NPC82623
0.7931	Intermediate Similarity	NPC159168
0.7931	Intermediate Similarity	NPC253402
0.7931	Intermediate Similarity	NPC134481
0.7927	Intermediate Similarity	NPC476366
0.7927	Intermediate Similarity	NPC471797
0.7927	Intermediate Similarity	NPC91858
0.7927	Intermediate Similarity	NPC201048
0.7907	Intermediate Similarity	NPC47761
0.7907	Intermediate Similarity	NPC142163
0.7907	Intermediate Similarity	NPC249423
0.7907	Intermediate Similarity	NPC264245
0.7901	Intermediate Similarity	NPC242001
0.7901	Intermediate Similarity	NPC110799
0.7901	Intermediate Similarity	NPC167706
0.7889	Intermediate Similarity	NPC471952
0.7882	Intermediate Similarity	NPC233295
0.7879	Intermediate Similarity	NPC301666
0.7872	Intermediate Similarity	NPC12103
0.7872	Intermediate Similarity	NPC227583
0.7872	Intermediate Similarity	NPC98457
0.7865	Intermediate Similarity	NPC237344
0.7865	Intermediate Similarity	NPC261266
0.7849	Intermediate Similarity	NPC65402
0.7849	Intermediate Similarity	NPC201725
0.7849	Intermediate Similarity	NPC144202
0.7849	Intermediate Similarity	NPC127718
0.7841	Intermediate Similarity	NPC205845
0.7841	Intermediate Similarity	NPC46320
0.7841	Intermediate Similarity	NPC474047
0.7841	Intermediate Similarity	NPC15534
0.7835	Intermediate Similarity	NPC273668
0.7831	Intermediate Similarity	NPC66566
0.7831	Intermediate Similarity	NPC477923
0.7831	Intermediate Similarity	NPC144075
0.7826	Intermediate Similarity	NPC41239
0.7826	Intermediate Similarity	NPC471453
0.7826	Intermediate Similarity	NPC477574
0.7816	Intermediate Similarity	NPC248886
0.7816	Intermediate Similarity	NPC87489
0.7805	Intermediate Similarity	NPC211009
0.7802	Intermediate Similarity	NPC470588
0.7802	Intermediate Similarity	NPC138974
0.7802	Intermediate Similarity	NPC20946
0.7802	Intermediate Similarity	NPC187785
0.7802	Intermediate Similarity	NPC259875
0.78	Intermediate Similarity	NPC38376
0.78	Intermediate Similarity	NPC80210
0.7791	Intermediate Similarity	NPC164840
0.7791	Intermediate Similarity	NPC241290
0.7791	Intermediate Similarity	NPC234193
0.7791	Intermediate Similarity	NPC474592
0.7791	Intermediate Similarity	NPC209944
0.7778	Intermediate Similarity	NPC131329
0.7778	Intermediate Similarity	NPC304083
0.7778	Intermediate Similarity	NPC73064
0.7778	Intermediate Similarity	NPC476948
0.7778	Intermediate Similarity	NPC145498
0.7766	Intermediate Similarity	NPC290481
0.7765	Intermediate Similarity	NPC285761
0.7755	Intermediate Similarity	NPC473124
0.7755	Intermediate Similarity	NPC473123
0.7753	Intermediate Similarity	NPC470360
0.7753	Intermediate Similarity	NPC133954
0.7753	Intermediate Similarity	NPC318390
0.7742	Intermediate Similarity	NPC307776
0.7738	Intermediate Similarity	NPC253190
0.7738	Intermediate Similarity	NPC470766
0.7732	Intermediate Similarity	NPC473160
0.7727	Intermediate Similarity	NPC132386
0.7727	Intermediate Similarity	NPC475789
0.7727	Intermediate Similarity	NPC52108
0.7727	Intermediate Similarity	NPC474789
0.7723	Intermediate Similarity	NPC195116
0.7723	Intermediate Similarity	NPC285253
0.7723	Intermediate Similarity	NPC221110
0.7723	Intermediate Similarity	NPC180459
0.7722	Intermediate Similarity	NPC42630
0.7717	Intermediate Similarity	NPC474728
0.7717	Intermediate Similarity	NPC192437
0.7717	Intermediate Similarity	NPC270511
0.7717	Intermediate Similarity	NPC14380
0.7717	Intermediate Similarity	NPC471433
0.7717	Intermediate Similarity	NPC470390
0.7717	Intermediate Similarity	NPC245410
0.7717	Intermediate Similarity	NPC471432
0.7701	Intermediate Similarity	NPC108476
0.7701	Intermediate Similarity	NPC195334
0.7701	Intermediate Similarity	NPC290495
0.7692	Intermediate Similarity	NPC246708
0.7692	Intermediate Similarity	NPC474512
0.7692	Intermediate Similarity	NPC212596
0.7692	Intermediate Similarity	NPC40552
0.7692	Intermediate Similarity	NPC470629
0.7692	Intermediate Similarity	NPC290690
0.7692	Intermediate Similarity	NPC181225
0.7692	Intermediate Similarity	NPC473242
0.7692	Intermediate Similarity	NPC475605
0.7692	Intermediate Similarity	NPC17733
0.7692	Intermediate Similarity	NPC4574
0.7684	Intermediate Similarity	NPC327179

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 NPC477578 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	2092
0.2-0.3	4000
0.3-0.4	2054
0.4-0.5	461
0.5-0.6	255
0.6-0.7	59
0.7-0.8	3
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8537	High Similarity	NPD7645	Phase 2
0.7586	Intermediate Similarity	NPD7525	Registered
0.7412	Intermediate Similarity	NPD7339	Approved
0.7412	Intermediate Similarity	NPD6942	Approved
0.7326	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7748	Approved
0.7263	Intermediate Similarity	NPD7515	Phase 2
0.7209	Intermediate Similarity	NPD8264	Approved
0.7172	Intermediate Similarity	NPD7638	Approved
0.71	Intermediate Similarity	NPD7639	Approved
0.71	Intermediate Similarity	NPD7640	Approved
0.7071	Intermediate Similarity	NPD7902	Approved
0.7021	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4784	Approved
0.6897	Remote Similarity	NPD6924	Approved
0.6897	Remote Similarity	NPD4785	Approved
0.6897	Remote Similarity	NPD6926	Approved
0.6882	Remote Similarity	NPD4786	Approved
0.6863	Remote Similarity	NPD4159	Approved
0.6848	Remote Similarity	NPD3667	Approved
0.6813	Remote Similarity	NPD4748	Discontinued
0.6778	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6695	Phase 3
0.6768	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD7900	Approved
0.6757	Remote Similarity	NPD7115	Discovery
0.6742	Remote Similarity	NPD6933	Approved
0.6737	Remote Similarity	NPD3618	Phase 1
0.6735	Remote Similarity	NPD6079	Approved
0.6702	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5328	Approved
0.6701	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD4243	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD7152	Approved
0.6667	Remote Similarity	NPD7151	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6635	Remote Similarity	NPD7632	Discontinued
0.6632	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.663	Remote Similarity	NPD7514	Phase 3
0.663	Remote Similarity	NPD6930	Phase 2
0.663	Remote Similarity	NPD7332	Phase 2
0.663	Remote Similarity	NPD6931	Approved
0.663	Remote Similarity	NPD7509	Discontinued
0.6579	Remote Similarity	NPD8294	Approved
0.6579	Remote Similarity	NPD8377	Approved
0.6552	Remote Similarity	NPD7143	Approved
0.6552	Remote Similarity	NPD7144	Approved
0.6549	Remote Similarity	NPD7328	Approved
0.6549	Remote Similarity	NPD7327	Approved
0.6522	Remote Similarity	NPD6929	Approved
0.6522	Remote Similarity	NPD7503	Approved
0.6522	Remote Similarity	NPD8378	Approved
0.6522	Remote Similarity	NPD8335	Approved
0.6522	Remote Similarity	NPD8380	Approved
0.6522	Remote Similarity	NPD8379	Approved
0.6522	Remote Similarity	NPD8296	Approved
0.65	Remote Similarity	NPD4202	Approved
0.65	Remote Similarity	NPD6399	Phase 3
0.6495	Remote Similarity	NPD7750	Discontinued
0.6495	Remote Similarity	NPD3573	Approved
0.6495	Remote Similarity	NPD7524	Approved
0.6491	Remote Similarity	NPD7516	Approved
0.6484	Remote Similarity	NPD6932	Approved
0.6437	Remote Similarity	NPD6923	Approved
0.6437	Remote Similarity	NPD6922	Approved
0.6437	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD7145	Approved
0.64	Remote Similarity	NPD8035	Phase 2
0.64	Remote Similarity	NPD6411	Approved
0.64	Remote Similarity	NPD8034	Phase 2
0.6386	Remote Similarity	NPD368	Approved
0.6383	Remote Similarity	NPD6902	Approved
0.6354	Remote Similarity	NPD3666	Approved
0.6354	Remote Similarity	NPD3665	Phase 1
0.6354	Remote Similarity	NPD3133	Approved
0.6344	Remote Similarity	NPD4195	Approved
0.633	Remote Similarity	NPD6881	Approved
0.633	Remote Similarity	NPD6899	Approved
0.633	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5211	Phase 2
0.6311	Remote Similarity	NPD5222	Approved
0.6311	Remote Similarity	NPD5221	Approved
0.6311	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD5776	Phase 2
0.6304	Remote Similarity	NPD6925	Approved
0.6296	Remote Similarity	NPD6675	Approved
0.6296	Remote Similarity	NPD7128	Approved
0.6296	Remote Similarity	NPD6402	Approved
0.6296	Remote Similarity	NPD5739	Approved
0.6289	Remote Similarity	NPD1694	Approved
0.6289	Remote Similarity	NPD6893	Approved
0.6286	Remote Similarity	NPD4696	Approved
0.6286	Remote Similarity	NPD5286	Approved
0.6286	Remote Similarity	NPD5285	Approved
0.6273	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD5275	Approved
0.6264	Remote Similarity	NPD4190	Phase 3
0.6263	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4755	Approved
0.625	Remote Similarity	NPD5173	Approved
0.6239	Remote Similarity	NPD5697	Approved
0.6238	Remote Similarity	NPD7087	Discontinued
0.6226	Remote Similarity	NPD5223	Approved
0.6226	Remote Similarity	NPD5344	Discontinued
0.6224	Remote Similarity	NPD4519	Discontinued
0.6224	Remote Similarity	NPD4623	Approved
0.6216	Remote Similarity	NPD7290	Approved
0.6216	Remote Similarity	NPD6883	Approved
0.6216	Remote Similarity	NPD7102	Approved
0.6211	Remote Similarity	NPD6898	Phase 1
0.6204	Remote Similarity	NPD5141	Approved
0.62	Remote Similarity	NPD6101	Approved
0.62	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5290	Discontinued
0.6186	Remote Similarity	NPD3668	Phase 3
0.6182	Remote Similarity	NPD6011	Approved
0.6182	Remote Similarity	NPD7320	Approved
0.618	Remote Similarity	NPD4787	Phase 1
0.6174	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6683	Phase 2
0.6168	Remote Similarity	NPD5226	Approved
0.6168	Remote Similarity	NPD4633	Approved
0.6168	Remote Similarity	NPD5225	Approved
0.6168	Remote Similarity	NPD5224	Approved
0.6167	Remote Similarity	NPD7507	Approved
0.6161	Remote Similarity	NPD6617	Approved
0.6161	Remote Similarity	NPD6650	Approved
0.6161	Remote Similarity	NPD6649	Approved
0.6161	Remote Similarity	NPD6869	Approved
0.6161	Remote Similarity	NPD6847	Approved
0.6161	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD4697	Phase 3
0.6132	Remote Similarity	NPD4700	Approved
0.6126	Remote Similarity	NPD6373	Approved
0.6126	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6014	Approved
0.6126	Remote Similarity	NPD6372	Approved
0.6126	Remote Similarity	NPD6012	Approved
0.6126	Remote Similarity	NPD6013	Approved
0.6111	Remote Similarity	NPD5174	Approved
0.6111	Remote Similarity	NPD5175	Approved
0.6106	Remote Similarity	NPD8297	Approved
0.6106	Remote Similarity	NPD6882	Approved
0.6105	Remote Similarity	NPD6928	Phase 2
0.6095	Remote Similarity	NPD6084	Phase 2
0.6095	Remote Similarity	NPD6083	Phase 2
0.6091	Remote Similarity	NPD5701	Approved
0.6078	Remote Similarity	NPD7637	Suspended
0.6071	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7146	Approved
0.6061	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5330	Approved
0.6061	Remote Similarity	NPD6409	Approved
0.6061	Remote Similarity	NPD6684	Approved
0.6061	Remote Similarity	NPD7334	Approved
0.6061	Remote Similarity	NPD7521	Approved
0.6053	Remote Similarity	NPD8133	Approved
0.604	Remote Similarity	NPD4753	Phase 2
0.6036	Remote Similarity	NPD6686	Approved
0.602	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5779	Approved
0.6019	Remote Similarity	NPD5778	Approved
0.6018	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD8328	Phase 3
0.5981	Remote Similarity	NPD6648	Approved
0.5979	Remote Similarity	NPD4223	Phase 3
0.5979	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD4221	Approved
0.5963	Remote Similarity	NPD4754	Approved
0.596	Remote Similarity	NPD5329	Approved
0.596	Remote Similarity	NPD1696	Phase 3
0.5946	Remote Similarity	NPD6412	Phase 2
0.5941	Remote Similarity	NPD6903	Approved
0.5938	Remote Similarity	NPD4695	Discontinued
0.5934	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4788	Approved
0.5905	Remote Similarity	NPD4629	Approved
0.5905	Remote Similarity	NPD5210	Approved
0.59	Remote Similarity	NPD5279	Phase 3
0.5893	Remote Similarity	NPD4730	Approved
0.5893	Remote Similarity	NPD4729	Approved
0.5889	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7741	Discontinued
0.5862	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD4197	Approved
0.5856	Remote Similarity	NPD4767	Approved
0.5856	Remote Similarity	NPD4768	Approved
0.5854	Remote Similarity	NPD342	Phase 1
0.5851	Remote Similarity	NPD6117	Approved
0.5847	Remote Similarity	NPD6335	Approved
0.5833	Remote Similarity	NPD8513	Phase 3
0.5833	Remote Similarity	NPD8515	Approved
0.5833	Remote Similarity	NPD8516	Approved
0.5833	Remote Similarity	NPD8517	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