NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	498.45
Volume:	570.609
LogP:	6.325
LogD:	5.578
LogS:	-5.08
# Rotatable Bonds:	8
TPSA:	26.71
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.364
Synthetic Accessibility Score:	5.104
Fsp3:	0.879
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:	-4.822
MDCK Permeability:	7.648871360288467e-06
Pgp-inhibitor:	0.97
Pgp-substrate:	0.096
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.899
30% Bioavailability (F30%):	0.749

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.7
Plasma Protein Binding (PPB):	83.69170379638672%
Volume Distribution (VD):	1.828
Pgp-substrate:	7.609418869018555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.136
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.992
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.148
CYP2D6-inhibitor:	0.851
CYP2D6-substrate:	0.947
CYP3A4-inhibitor:	0.83
CYP3A4-substrate:	0.913

ADMET: Excretion

Clearance (CL):	7.094
Half-life (T1/2):	0.086

ADMET: Toxicity

hERG Blockers:	0.17
Human Hepatotoxicity (H-HT):	0.4
Drug-inuced Liver Injury (DILI):	0.093
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.4
Maximum Recommended Daily Dose:	0.24
Skin Sensitization:	0.921
Carcinogencity:	0.034
Eye Corrosion:	0.195
Eye Irritation:	0.022
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC476903

Natural Product ID:	NPC476903
*Common Name:**	(2S,3S,5S,9R,10S,13R,14R,17R)-3-(dimethylamino)-17-[(Z,2R)-5-[2-(dimethylamino)ethyl]-6-methylhept-4-en-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-2-ol
IUPAC Name:	(2S,3S,5S,9R,10S,13R,14R,17R)-3-(dimethylamino)-17-[(Z,2R)-5-[2-(dimethylamino)ethyl]-6-methylhept-4-en-2-yl]-10,13-dimethyl-2,3,4,5,6,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-2-ol
Synonyms:
Standard InCHIKey:	KZTQGTBWBPDHGD-ACWZIQGQSA-N
Standard InCHI:	InChI=1S/C33H58N2O/c1-22(2)24(17-19-34(6)7)11-10-23(3)27-14-15-28-26-13-12-25-20-30(35(8)9)31(36)21-33(25,5)29(26)16-18-32(27,28)4/h11,13,22-23,25,27-31,36H,10,12,14-21H2,1-9H3/b24-11-/t23-,25+,27-,28+,29+,30+,31+,32-,33+/m1/s1
SMILES:	C[C@H](C/C=C(/CCN(C)C)\C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3C2=CC[C@@H]4[C@@]3(C[C@@H]([C@H](C4)N(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	76317102
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes and derivatives

*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
NPO32780	corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12193035]
NPO32780	corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17391049]
NPO32780	corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	New Britain, Papua New Guinea	n.a.	PMID[24195491]
NPO32780	corticium sp.	Species	Corticiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964780]

☑ 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
MIC	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT115	Organism	Mycobacterium tuberculosis H37Ra	Mycobacterium tuberculosis H37Ra	MIC	=	15.8	ug/ml	PMID[24195491]

☑ 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 NPC476903 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	91
0.1-0.2	917
0.2-0.3	11638
0.3-0.4	15221
0.4-0.5	8243
0.5-0.6	5338
0.6-0.7	1061
0.7-0.8	176
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8969	High Similarity	NPC241879
0.87	High Similarity	NPC25340
0.8673	High Similarity	NPC471083
0.8462	Intermediate Similarity	NPC75810
0.8431	Intermediate Similarity	NPC159367
0.8351	Intermediate Similarity	NPC289140
0.83	Intermediate Similarity	NPC50815
0.8286	Intermediate Similarity	NPC56796
0.8265	Intermediate Similarity	NPC140300
0.8247	Intermediate Similarity	NPC272732
0.8247	Intermediate Similarity	NPC311164
0.8235	Intermediate Similarity	NPC55462
0.8218	Intermediate Similarity	NPC474583
0.8182	Intermediate Similarity	NPC91604
0.8119	Intermediate Similarity	NPC247060
0.8095	Intermediate Similarity	NPC472359
0.8081	Intermediate Similarity	NPC474164
0.7921	Intermediate Similarity	NPC135799
0.7843	Intermediate Similarity	NPC118275
0.781	Intermediate Similarity	NPC46981
0.7788	Intermediate Similarity	NPC475239
0.7778	Intermediate Similarity	NPC280710
0.7778	Intermediate Similarity	NPC243985
0.7767	Intermediate Similarity	NPC176012
0.7753	Intermediate Similarity	NPC471723
0.7753	Intermediate Similarity	NPC141071
0.7753	Intermediate Similarity	NPC257347
0.7723	Intermediate Similarity	NPC240650
0.7706	Intermediate Similarity	NPC478137
0.7685	Intermediate Similarity	NPC474459
0.7677	Intermediate Similarity	NPC93027
0.7667	Intermediate Similarity	NPC189883
0.7667	Intermediate Similarity	NPC134330
0.7667	Intermediate Similarity	NPC129165
0.7653	Intermediate Similarity	NPC84171
0.764	Intermediate Similarity	NPC476904
0.7619	Intermediate Similarity	NPC212874
0.7615	Intermediate Similarity	NPC474452
0.7573	Intermediate Similarity	NPC275686
0.7556	Intermediate Similarity	NPC288035
0.7556	Intermediate Similarity	NPC134847
0.7556	Intermediate Similarity	NPC22105
0.7556	Intermediate Similarity	NPC304309
0.7556	Intermediate Similarity	NPC136188
0.7556	Intermediate Similarity	NPC162742
0.7556	Intermediate Similarity	NPC285893
0.7556	Intermediate Similarity	NPC28657
0.7556	Intermediate Similarity	NPC230301
0.7547	Intermediate Similarity	NPC86906
0.7473	Intermediate Similarity	NPC321016
0.7473	Intermediate Similarity	NPC202642
0.7473	Intermediate Similarity	NPC240604
0.7473	Intermediate Similarity	NPC321381
0.7473	Intermediate Similarity	NPC237460
0.7473	Intermediate Similarity	NPC300324
0.7473	Intermediate Similarity	NPC113733
0.7473	Intermediate Similarity	NPC107059
0.7473	Intermediate Similarity	NPC46160
0.7473	Intermediate Similarity	NPC470362
0.7455	Intermediate Similarity	NPC80834
0.7455	Intermediate Similarity	NPC469968
0.7431	Intermediate Similarity	NPC472313
0.7419	Intermediate Similarity	NPC30986
0.7419	Intermediate Similarity	NPC1319
0.7419	Intermediate Similarity	NPC209430
0.7416	Intermediate Similarity	NPC21773
0.7391	Intermediate Similarity	NPC34019
0.7391	Intermediate Similarity	NPC198968
0.7391	Intermediate Similarity	NPC214570
0.7391	Intermediate Similarity	NPC155986
0.7391	Intermediate Similarity	NPC242692
0.7391	Intermediate Similarity	NPC318495
0.7363	Intermediate Similarity	NPC322353
0.7363	Intermediate Similarity	NPC121744
0.7363	Intermediate Similarity	NPC118508
0.7358	Intermediate Similarity	NPC293299
0.7358	Intermediate Similarity	NPC45365
0.7358	Intermediate Similarity	NPC90538
0.734	Intermediate Similarity	NPC236112
0.7328	Intermediate Similarity	NPC472458
0.7312	Intermediate Similarity	NPC205455
0.7312	Intermediate Similarity	NPC65897
0.7312	Intermediate Similarity	NPC85346
0.7312	Intermediate Similarity	NPC244385
0.7312	Intermediate Similarity	NPC138621
0.7312	Intermediate Similarity	NPC18603
0.7312	Intermediate Similarity	NPC477522
0.7312	Intermediate Similarity	NPC285761
0.7312	Intermediate Similarity	NPC167037
0.7312	Intermediate Similarity	NPC474216
0.7312	Intermediate Similarity	NPC473943
0.7312	Intermediate Similarity	NPC186191
0.7312	Intermediate Similarity	NPC76931
0.7312	Intermediate Similarity	NPC302041
0.7312	Intermediate Similarity	NPC307965
0.7312	Intermediate Similarity	NPC87604
0.7312	Intermediate Similarity	NPC6978
0.7312	Intermediate Similarity	NPC275910
0.729	Intermediate Similarity	NPC470596
0.7283	Intermediate Similarity	NPC73875
0.7283	Intermediate Similarity	NPC244488
0.7283	Intermediate Similarity	NPC247325
0.7264	Intermediate Similarity	NPC476755
0.7263	Intermediate Similarity	NPC474531
0.7263	Intermediate Similarity	NPC109533
0.7253	Intermediate Similarity	NPC469534
0.7253	Intermediate Similarity	NPC469533
0.7253	Intermediate Similarity	NPC469593
0.7234	Intermediate Similarity	NPC328714
0.7234	Intermediate Similarity	NPC81306
0.7234	Intermediate Similarity	NPC273410
0.7234	Intermediate Similarity	NPC80530
0.7234	Intermediate Similarity	NPC109546
0.7234	Intermediate Similarity	NPC28862
0.7234	Intermediate Similarity	NPC47982
0.7234	Intermediate Similarity	NPC84694
0.7234	Intermediate Similarity	NPC143182
0.7222	Intermediate Similarity	NPC36497
0.7207	Intermediate Similarity	NPC79238
0.7196	Intermediate Similarity	NPC98765
0.7188	Intermediate Similarity	NPC215474
0.7188	Intermediate Similarity	NPC30166
0.7188	Intermediate Similarity	NPC470049
0.7182	Intermediate Similarity	NPC147835
0.7182	Intermediate Similarity	NPC85001
0.7182	Intermediate Similarity	NPC95920
0.7182	Intermediate Similarity	NPC253645
0.7158	Intermediate Similarity	NPC209944
0.7158	Intermediate Similarity	NPC26117
0.7158	Intermediate Similarity	NPC164840
0.7158	Intermediate Similarity	NPC236237
0.7158	Intermediate Similarity	NPC241290
0.7158	Intermediate Similarity	NPC102253
0.7158	Intermediate Similarity	NPC234193
0.7158	Intermediate Similarity	NPC322313
0.7158	Intermediate Similarity	NPC13554
0.7156	Intermediate Similarity	NPC169375
0.7143	Intermediate Similarity	NPC201373
0.7143	Intermediate Similarity	NPC124358
0.7143	Intermediate Similarity	NPC474140
0.7143	Intermediate Similarity	NPC182717
0.7143	Intermediate Similarity	NPC152684
0.7128	Intermediate Similarity	NPC318136
0.7128	Intermediate Similarity	NPC312328
0.7128	Intermediate Similarity	NPC477514
0.7113	Intermediate Similarity	NPC317458
0.7105	Intermediate Similarity	NPC28280
0.7105	Intermediate Similarity	NPC304646
0.7105	Intermediate Similarity	NPC165396
0.7097	Intermediate Similarity	NPC7214
0.7097	Intermediate Similarity	NPC96319
0.7091	Intermediate Similarity	NPC470595
0.7083	Intermediate Similarity	NPC470383
0.7083	Intermediate Similarity	NPC82986
0.7083	Intermediate Similarity	NPC47761
0.7083	Intermediate Similarity	NPC474731
0.7083	Intermediate Similarity	NPC474759
0.7083	Intermediate Similarity	NPC474683
0.7083	Intermediate Similarity	NPC7505
0.7083	Intermediate Similarity	NPC23852
0.7083	Intermediate Similarity	NPC474752
0.7083	Intermediate Similarity	NPC209620
0.7083	Intermediate Similarity	NPC264245
0.7079	Intermediate Similarity	NPC160209
0.7071	Intermediate Similarity	NPC166458
0.7065	Intermediate Similarity	NPC100334
0.7048	Intermediate Similarity	NPC292819
0.7041	Intermediate Similarity	NPC478102
0.7041	Intermediate Similarity	NPC124172
0.7041	Intermediate Similarity	NPC209802
0.7041	Intermediate Similarity	NPC474047
0.7041	Intermediate Similarity	NPC470077
0.7037	Intermediate Similarity	NPC473254
0.7033	Intermediate Similarity	NPC111234
0.7033	Intermediate Similarity	NPC265789
0.701	Intermediate Similarity	NPC87489
0.701	Intermediate Similarity	NPC189972
0.701	Intermediate Similarity	NPC470614
0.701	Intermediate Similarity	NPC50964
0.701	Intermediate Similarity	NPC202389
0.701	Intermediate Similarity	NPC248886
0.701	Intermediate Similarity	NPC101462
0.701	Intermediate Similarity	NPC5985
0.701	Intermediate Similarity	NPC1272
0.701	Intermediate Similarity	NPC201852
0.701	Intermediate Similarity	NPC296701
0.701	Intermediate Similarity	NPC218616
0.701	Intermediate Similarity	NPC20853
0.701	Intermediate Similarity	NPC49964
0.6989	Remote Similarity	NPC200243
0.6972	Remote Similarity	NPC119329
0.697	Remote Similarity	NPC157257
0.697	Remote Similarity	NPC318390
0.6957	Remote Similarity	NPC471799
0.6957	Remote Similarity	NPC195489
0.6939	Remote Similarity	NPC475789
0.6939	Remote Similarity	NPC474634
0.6939	Remote Similarity	NPC207013
0.6939	Remote Similarity	NPC113978
0.6939	Remote Similarity	NPC477818

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 NPC476903 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	100
0.1-0.2	510
0.2-0.3	3626
0.3-0.4	3453
0.4-0.5	1042
0.5-0.6	314
0.6-0.7	101
0.7-0.8	4
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
0.7556	Intermediate Similarity	NPD6942	Approved
0.7556	Intermediate Similarity	NPD7339	Approved
0.7158	Intermediate Similarity	NPD7525	Registered
0.7097	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7754	Approved
0.6957	Remote Similarity	NPD7755	Approved
0.6923	Remote Similarity	NPD5771	Approved
0.6869	Remote Similarity	NPD4786	Approved
0.6848	Remote Similarity	NPD4243	Approved
0.6729	Remote Similarity	NPD7920	Phase 3
0.6729	Remote Similarity	NPD7919	Phase 3
0.6702	Remote Similarity	NPD6926	Approved
0.6702	Remote Similarity	NPD6924	Approved
0.6702	Remote Similarity	NPD4785	Approved
0.6702	Remote Similarity	NPD4784	Approved
0.6701	Remote Similarity	NPD7645	Phase 2
0.6699	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD7150	Approved
0.6667	Remote Similarity	NPD3667	Approved
0.6667	Remote Similarity	NPD8088	Phase 1
0.6667	Remote Similarity	NPD7151	Approved
0.6667	Remote Similarity	NPD7152	Approved
0.663	Remote Similarity	NPD6923	Approved
0.663	Remote Similarity	NPD6922	Approved
0.6607	Remote Similarity	NPD6920	Discontinued
0.6571	Remote Similarity	NPD6079	Approved
0.6569	Remote Similarity	NPD3618	Phase 1
0.6562	Remote Similarity	NPD6933	Approved
0.6559	Remote Similarity	NPD7144	Approved
0.6559	Remote Similarity	NPD7143	Approved
0.6552	Remote Similarity	NPD8077	Approved
0.6552	Remote Similarity	NPD7335	Phase 2
0.6552	Remote Similarity	NPD7337	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7336	Phase 2
0.6552	Remote Similarity	NPD8078	Approved
0.6549	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6909	Approved
0.6529	Remote Similarity	NPD6908	Approved
0.6505	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6415	Discontinued
0.6465	Remote Similarity	NPD4748	Discontinued
0.646	Remote Similarity	NPD7333	Discontinued
0.6458	Remote Similarity	NPD4190	Phase 3
0.6458	Remote Similarity	NPD5275	Approved
0.6373	Remote Similarity	NPD3133	Approved
0.6373	Remote Similarity	NPD3665	Phase 1
0.6373	Remote Similarity	NPD3666	Approved
0.6364	Remote Similarity	NPD6929	Approved
0.6356	Remote Similarity	NPD8298	Phase 2
0.6355	Remote Similarity	NPD4202	Approved
0.633	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.63	Remote Similarity	NPD7509	Discontinued
0.63	Remote Similarity	NPD6930	Phase 2
0.63	Remote Similarity	NPD6931	Approved
0.6286	Remote Similarity	NPD4723	Approved
0.6286	Remote Similarity	NPD4722	Approved
0.6283	Remote Similarity	NPD7911	Approved
0.6283	Remote Similarity	NPD7987	Approved
0.6283	Remote Similarity	NPD7912	Approved
0.6283	Remote Similarity	NPD7986	Approved
0.6204	Remote Similarity	NPD6399	Phase 3
0.62	Remote Similarity	NPD4195	Approved
0.6182	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5222	Approved
0.6182	Remote Similarity	NPD4697	Phase 3
0.6182	Remote Similarity	NPD5221	Approved
0.6174	Remote Similarity	NPD8040	Discontinued
0.6162	Remote Similarity	NPD6932	Approved
0.6162	Remote Similarity	NPD5776	Phase 2
0.6162	Remote Similarity	NPD6925	Approved
0.6161	Remote Similarity	NPD8418	Phase 2
0.6154	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD8449	Approved
0.6126	Remote Similarity	NPD5173	Approved
0.6126	Remote Similarity	NPD4755	Approved
0.6122	Remote Similarity	NPD8264	Approved
0.6121	Remote Similarity	NPD7989	Approved
0.6121	Remote Similarity	NPD7990	Approved
0.6117	Remote Similarity	NPD6695	Phase 3
0.6107	Remote Similarity	NPD8450	Suspended
0.61	Remote Similarity	NPD7145	Approved
0.6098	Remote Similarity	NPD7522	Discontinued
0.6095	Remote Similarity	NPD8308	Discontinued
0.6095	Remote Similarity	NPD5279	Phase 3
0.6091	Remote Similarity	NPD7991	Discontinued
0.6075	Remote Similarity	NPD4753	Phase 2
0.6058	Remote Similarity	NPD3668	Phase 3
0.6058	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.604	Remote Similarity	NPD6683	Phase 2
0.6038	Remote Similarity	NPD7750	Discontinued
0.6019	Remote Similarity	NPD4223	Phase 3
0.6019	Remote Similarity	NPD4221	Approved
0.6018	Remote Similarity	NPD4700	Approved
0.6018	Remote Similarity	NPD5285	Approved
0.6018	Remote Similarity	NPD4696	Approved
0.6018	Remote Similarity	NPD5286	Approved
0.6	Remote Similarity	NPD6893	Approved
0.6	Remote Similarity	NPD5329	Approved
0.6	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7514	Phase 3
0.5965	Remote Similarity	NPD5223	Approved
0.5963	Remote Similarity	NPD7515	Phase 2
0.5941	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5929	Remote Similarity	NPD5290	Discontinued
0.5929	Remote Similarity	NPD7638	Approved
0.5922	Remote Similarity	NPD6902	Approved
0.5913	Remote Similarity	NPD5226	Approved
0.5913	Remote Similarity	NPD4633	Approved
0.5913	Remote Similarity	NPD5224	Approved
0.5913	Remote Similarity	NPD5211	Phase 2
0.5913	Remote Similarity	NPD4719	Phase 2
0.5913	Remote Similarity	NPD5225	Approved
0.5905	Remote Similarity	NPD4197	Approved
0.5897	Remote Similarity	NPD7128	Approved
0.5897	Remote Similarity	NPD6675	Approved
0.5897	Remote Similarity	NPD5739	Approved
0.5897	Remote Similarity	NPD6402	Approved
0.5888	Remote Similarity	NPD7524	Approved
0.5877	Remote Similarity	NPD7639	Approved
0.5877	Remote Similarity	NPD7640	Approved
0.5876	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD6939	Phase 2
0.5862	Remote Similarity	NPD4754	Approved
0.5862	Remote Similarity	NPD5175	Approved
0.5862	Remote Similarity	NPD5174	Approved
0.5856	Remote Similarity	NPD7748	Approved
0.5841	Remote Similarity	NPD6084	Phase 2
0.5841	Remote Similarity	NPD6083	Phase 2
0.5826	Remote Similarity	NPD4159	Approved
0.5825	Remote Similarity	NPD7332	Phase 2
0.5818	Remote Similarity	NPD8034	Phase 2
0.5818	Remote Similarity	NPD8035	Phase 2
0.5812	Remote Similarity	NPD5141	Approved
0.581	Remote Similarity	NPD4788	Approved
0.5804	Remote Similarity	NPD5210	Approved
0.5804	Remote Similarity	NPD4629	Approved
0.5798	Remote Similarity	NPD7320	Approved
0.5798	Remote Similarity	NPD6899	Approved
0.5798	Remote Similarity	NPD6881	Approved
0.5794	Remote Similarity	NPD6409	Approved
0.5794	Remote Similarity	NPD4693	Phase 3
0.5794	Remote Similarity	NPD7146	Approved
0.5794	Remote Similarity	NPD7334	Approved
0.5794	Remote Similarity	NPD4689	Approved
0.5794	Remote Similarity	NPD6684	Approved
0.5794	Remote Similarity	NPD4688	Approved
0.5794	Remote Similarity	NPD5205	Approved
0.5794	Remote Similarity	NPD4690	Approved
0.5794	Remote Similarity	NPD4138	Approved
0.5794	Remote Similarity	NPD5330	Approved
0.5794	Remote Similarity	NPD7521	Approved
0.5785	Remote Similarity	NPD8130	Phase 1
0.5781	Remote Similarity	NPD7122	Discontinued
0.578	Remote Similarity	NPD6051	Approved
0.5775	Remote Similarity	NPD8131	Suspended
0.5773	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6898	Phase 1
0.5763	Remote Similarity	NPD4768	Approved
0.5763	Remote Similarity	NPD4767	Approved
0.575	Remote Similarity	NPD6372	Approved
0.575	Remote Similarity	NPD6373	Approved
0.5743	Remote Similarity	NPD1346	Approved
0.5739	Remote Similarity	NPD6404	Discontinued
0.5738	Remote Similarity	NPD8297	Approved
0.5727	Remote Similarity	NPD4096	Approved
0.5714	Remote Similarity	NPD4787	Phase 1
0.5714	Remote Similarity	NPD5697	Approved
0.5714	Remote Similarity	NPD5701	Approved
0.5714	Remote Similarity	NPD5707	Approved
0.5702	Remote Similarity	NPD7902	Approved
0.5702	Remote Similarity	NPD6883	Approved
0.5702	Remote Similarity	NPD7290	Approved
0.5702	Remote Similarity	NPD7102	Approved
0.5688	Remote Similarity	NPD6903	Approved
0.5688	Remote Similarity	NPD5737	Approved
0.5688	Remote Similarity	NPD6672	Approved
0.5688	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD7087	Discontinued
0.567	Remote Similarity	NPD6705	Phase 1
0.5667	Remote Similarity	NPD8174	Phase 2
0.5667	Remote Similarity	NPD4730	Approved
0.5667	Remote Similarity	NPD6011	Approved
0.5667	Remote Similarity	NPD4729	Approved
0.5667	Remote Similarity	NPD5128	Approved
0.5667	Remote Similarity	NPD5168	Approved
0.5657	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6869	Approved
0.5656	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5656	Remote Similarity	NPD6847	Approved
0.5656	Remote Similarity	NPD6617	Approved
0.5656	Remote Similarity	NPD6649	Approved
0.5656	Remote Similarity	NPD6650	Approved
0.5648	Remote Similarity	NPD5280	Approved
0.5648	Remote Similarity	NPD5690	Phase 2
0.5648	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD4694	Approved
0.5634	Remote Similarity	NPD3638	Discontinued
0.5631	Remote Similarity	NPD3617	Approved
0.563	Remote Similarity	NPD6640	Phase 3

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data