NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	500.35
Volume:	543.911
LogP:	4.671
LogD:	4.026
LogS:	-4.074
# Rotatable Bonds:	6
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.361
Synthetic Accessibility Score:	5.342
Fsp3:	0.774
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.205
MDCK Permeability:	2.0331519408500753e-05
Pgp-inhibitor:	0.483
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.101
30% Bioavailability (F30%):	0.045

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.084
Plasma Protein Binding (PPB):	92.02543640136719%
Volume Distribution (VD):	0.603
Pgp-substrate:	6.009091854095459%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.006
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.819
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.231
CYP3A4-inhibitor:	0.037
CYP3A4-substrate:	0.283

ADMET: Excretion

Clearance (CL):	3.967
Half-life (T1/2):	0.659

ADMET: Toxicity

hERG Blockers:	0.066
Human Hepatotoxicity (H-HT):	0.54
Drug-inuced Liver Injury (DILI):	0.006
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.687
Maximum Recommended Daily Dose:	0.945
Skin Sensitization:	0.593
Carcinogencity:	0.218
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC477812

Natural Product ID:	NPC477812
*Common Name:**	15alpha-Hydroxytumulosic acid
IUPAC Name:	6-methyl-5-methylidene-2-[(3S,5R,10S,13R,14R,15R,16S,17R)-3,15,16-trihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]heptanoic acid
Synonyms:	15-alpha-hydroxydehydrotumulosic acid
Standard InCHIKey:	WTFURVULOVLFRN-YZBXQDNMSA-N
Standard InCHI:	InChI=1S/C31H48O5/c1-17(2)18(3)9-10-19(27(35)36)24-25(33)26(34)31(8)21-11-12-22-28(4,5)23(32)14-15-29(22,6)20(21)13-16-30(24,31)7/h11,13,17,19,22-26,32-34H,3,9-10,12,14-16H2,1-2,4-8H3,(H,35,36)/t19?,22-,23-,24-,25-,26-,29+,30+,31+/m0/s1
SMILES:	CC(C)C(=C)CCC([C@H]1[C@@H]([C@@H]([C@@]2([C@@]1(CC=C3C2=CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C)O)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	16736459
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001104] Trihydroxy bile acids, alcohols 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
NPO33546	Poria coco	Species		Eukaryota	n.a.	Yunnan, Kunming, China	n.a.	PMID[17488130]

☑ 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	5

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	22.5	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	70	%	PMID[17488130]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	91	%	PMID[17488130]

☑ 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 NPC477812 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	197
0.1-0.2	1075
0.2-0.3	4298
0.3-0.4	10131
0.4-0.5	12051
0.5-0.6	6739
0.6-0.7	6245
0.7-0.8	1761
0.8-0.85	157
0.85-0.9	33
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9271	High Similarity	NPC173272
0.9167	High Similarity	NPC162001
0.9167	High Similarity	NPC45324
0.9167	High Similarity	NPC48330
0.9167	High Similarity	NPC222845
0.8889	High Similarity	NPC186810
0.8889	High Similarity	NPC477813
0.8889	High Similarity	NPC48647
0.8854	High Similarity	NPC23434
0.8763	High Similarity	NPC206810
0.8763	High Similarity	NPC66429
0.8763	High Similarity	NPC470376
0.8763	High Similarity	NPC152897
0.8763	High Similarity	NPC470375
0.87	High Similarity	NPC477854
0.8687	High Similarity	NPC477853
0.8646	High Similarity	NPC77168
0.8646	High Similarity	NPC84271
0.8646	High Similarity	NPC102414
0.8614	High Similarity	NPC316964
0.86	High Similarity	NPC190554
0.8586	High Similarity	NPC127063
0.8586	High Similarity	NPC69548
0.8586	High Similarity	NPC263347
0.8586	High Similarity	NPC184848
0.8558	High Similarity	NPC231530
0.8558	High Similarity	NPC323834
0.8558	High Similarity	NPC278628
0.8557	High Similarity	NPC46281
0.8544	High Similarity	NPC191892
0.8544	High Similarity	NPC55872
0.8544	High Similarity	NPC140723
0.8542	High Similarity	NPC242864
0.8542	High Similarity	NPC48866
0.8542	High Similarity	NPC247406
0.85	High Similarity	NPC155676
0.85	High Similarity	NPC95565
0.8485	Intermediate Similarity	NPC166906
0.8485	Intermediate Similarity	NPC469406
0.8476	Intermediate Similarity	NPC475060
0.8476	Intermediate Similarity	NPC59530
0.8476	Intermediate Similarity	NPC220229
0.8469	Intermediate Similarity	NPC189520
0.8462	Intermediate Similarity	NPC96268
0.8462	Intermediate Similarity	NPC28656
0.8462	Intermediate Similarity	NPC471293
0.8454	Intermediate Similarity	NPC54689
0.8447	Intermediate Similarity	NPC195290
0.8447	Intermediate Similarity	NPC204450
0.8438	Intermediate Similarity	NPC159046
0.8438	Intermediate Similarity	NPC233836
0.8438	Intermediate Similarity	NPC187376
0.8438	Intermediate Similarity	NPC312215
0.8431	Intermediate Similarity	NPC218383
0.8431	Intermediate Similarity	NPC15390
0.8426	Intermediate Similarity	NPC280782
0.8416	Intermediate Similarity	NPC469432
0.8411	Intermediate Similarity	NPC6206
0.8411	Intermediate Similarity	NPC197428
0.84	Intermediate Similarity	NPC470016
0.84	Intermediate Similarity	NPC317586
0.84	Intermediate Similarity	NPC469599
0.8396	Intermediate Similarity	NPC217201
0.8396	Intermediate Similarity	NPC65941
0.8396	Intermediate Similarity	NPC94529
0.8384	Intermediate Similarity	NPC477855
0.8381	Intermediate Similarity	NPC319077
0.8381	Intermediate Similarity	NPC260268
0.8381	Intermediate Similarity	NPC152695
0.8381	Intermediate Similarity	NPC476027
0.8381	Intermediate Similarity	NPC85829
0.8381	Intermediate Similarity	NPC171137
0.8381	Intermediate Similarity	NPC149047
0.8381	Intermediate Similarity	NPC49958
0.8381	Intermediate Similarity	NPC202167
0.8381	Intermediate Similarity	NPC48733
0.8381	Intermediate Similarity	NPC97202
0.8381	Intermediate Similarity	NPC214264
0.8381	Intermediate Similarity	NPC296945
0.8381	Intermediate Similarity	NPC50692
0.8381	Intermediate Similarity	NPC302607
0.8381	Intermediate Similarity	NPC150531
0.8367	Intermediate Similarity	NPC123854
0.8367	Intermediate Similarity	NPC107189
0.8367	Intermediate Similarity	NPC289213
0.8365	Intermediate Similarity	NPC236390
0.8365	Intermediate Similarity	NPC159442
0.8351	Intermediate Similarity	NPC294480
0.8349	Intermediate Similarity	NPC962
0.8349	Intermediate Similarity	NPC250109
0.8333	Intermediate Similarity	NPC28252
0.8333	Intermediate Similarity	NPC212843
0.8333	Intermediate Similarity	NPC55309
0.8333	Intermediate Similarity	NPC114274
0.8318	Intermediate Similarity	NPC10064
0.8318	Intermediate Similarity	NPC170221
0.8318	Intermediate Similarity	NPC11710
0.8317	Intermediate Similarity	NPC42042
0.8317	Intermediate Similarity	NPC305483
0.8317	Intermediate Similarity	NPC328162
0.8317	Intermediate Similarity	NPC96859
0.8302	Intermediate Similarity	NPC165873
0.8302	Intermediate Similarity	NPC83744
0.8302	Intermediate Similarity	NPC64844
0.8302	Intermediate Similarity	NPC42847
0.83	Intermediate Similarity	NPC49670
0.83	Intermediate Similarity	NPC111015
0.8286	Intermediate Similarity	NPC204833
0.8286	Intermediate Similarity	NPC209502
0.8286	Intermediate Similarity	NPC29705
0.8283	Intermediate Similarity	NPC154101
0.8283	Intermediate Similarity	NPC26888
0.8283	Intermediate Similarity	NPC45269
0.8283	Intermediate Similarity	NPC297265
0.8273	Intermediate Similarity	NPC473898
0.8269	Intermediate Similarity	NPC193934
0.8269	Intermediate Similarity	NPC271980
0.8269	Intermediate Similarity	NPC473424
0.8265	Intermediate Similarity	NPC474704
0.8265	Intermediate Similarity	NPC475921
0.8257	Intermediate Similarity	NPC71348
0.8252	Intermediate Similarity	NPC110149
0.8247	Intermediate Similarity	NPC474684
0.8247	Intermediate Similarity	NPC142361
0.8247	Intermediate Similarity	NPC477926
0.8241	Intermediate Similarity	NPC210005
0.8235	Intermediate Similarity	NPC108078
0.8235	Intermediate Similarity	NPC475033
0.8235	Intermediate Similarity	NPC320306
0.8235	Intermediate Similarity	NPC475032
0.8235	Intermediate Similarity	NPC43686
0.8224	Intermediate Similarity	NPC329417
0.8218	Intermediate Similarity	NPC473240
0.8218	Intermediate Similarity	NPC200702
0.8218	Intermediate Similarity	NPC472485
0.82	Intermediate Similarity	NPC243866
0.82	Intermediate Similarity	NPC25750
0.8198	Intermediate Similarity	NPC266728
0.8198	Intermediate Similarity	NPC49492
0.819	Intermediate Similarity	NPC117185
0.8182	Intermediate Similarity	NPC148414
0.8182	Intermediate Similarity	NPC202889
0.8182	Intermediate Similarity	NPC175628
0.8182	Intermediate Similarity	NPC111585
0.8182	Intermediate Similarity	NPC136801
0.8182	Intermediate Similarity	NPC194100
0.8182	Intermediate Similarity	NPC469400
0.8165	Intermediate Similarity	NPC188738
0.8163	Intermediate Similarity	NPC183546
0.8163	Intermediate Similarity	NPC470542
0.8155	Intermediate Similarity	NPC197386
0.8155	Intermediate Similarity	NPC166745
0.8155	Intermediate Similarity	NPC471717
0.8155	Intermediate Similarity	NPC10364
0.8155	Intermediate Similarity	NPC235464
0.8144	Intermediate Similarity	NPC155011
0.8142	Intermediate Similarity	NPC305260
0.8142	Intermediate Similarity	NPC475041
0.8142	Intermediate Similarity	NPC270850
0.8137	Intermediate Similarity	NPC88847
0.8137	Intermediate Similarity	NPC476327
0.8137	Intermediate Similarity	NPC476318
0.8137	Intermediate Similarity	NPC49371
0.8131	Intermediate Similarity	NPC477916
0.8131	Intermediate Similarity	NPC472925
0.8119	Intermediate Similarity	NPC470958
0.8119	Intermediate Similarity	NPC7165
0.8119	Intermediate Similarity	NPC470957
0.81	Intermediate Similarity	NPC110657
0.81	Intermediate Similarity	NPC19114
0.81	Intermediate Similarity	NPC86266
0.81	Intermediate Similarity	NPC212301
0.8095	Intermediate Similarity	NPC136289
0.8095	Intermediate Similarity	NPC293753
0.8095	Intermediate Similarity	NPC22388
0.8095	Intermediate Similarity	NPC234892
0.8095	Intermediate Similarity	NPC473928
0.8095	Intermediate Similarity	NPC477915
0.8091	Intermediate Similarity	NPC126691
0.8081	Intermediate Similarity	NPC155479
0.8081	Intermediate Similarity	NPC86319
0.8081	Intermediate Similarity	NPC476733
0.8081	Intermediate Similarity	NPC474679
0.8081	Intermediate Similarity	NPC32830
0.8081	Intermediate Similarity	NPC215029
0.8081	Intermediate Similarity	NPC474889
0.8081	Intermediate Similarity	NPC275740
0.8077	Intermediate Similarity	NPC83709
0.8077	Intermediate Similarity	NPC208358
0.8077	Intermediate Similarity	NPC205899
0.8077	Intermediate Similarity	NPC154072
0.8077	Intermediate Similarity	NPC327431
0.807	Intermediate Similarity	NPC79579
0.8061	Intermediate Similarity	NPC271967
0.8058	Intermediate Similarity	NPC43747
0.8058	Intermediate Similarity	NPC18319
0.8058	Intermediate Similarity	NPC189880
0.8056	Intermediate Similarity	NPC472219
0.8056	Intermediate Similarity	NPC472218
0.8056	Intermediate Similarity	NPC472217

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 NPC477812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1408
0.2-0.3	3847
0.3-0.4	2474
0.4-0.5	732
0.5-0.6	218
0.6-0.7	190
0.7-0.8	117
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
0.8037	Intermediate Similarity	NPD7128	Approved
0.8037	Intermediate Similarity	NPD5739	Approved
0.8037	Intermediate Similarity	NPD6675	Approved
0.8037	Intermediate Similarity	NPD6402	Approved
0.802	Intermediate Similarity	NPD6399	Phase 3
0.8018	Intermediate Similarity	NPD4632	Approved
0.7982	Intermediate Similarity	NPD6372	Approved
0.7982	Intermediate Similarity	NPD6373	Approved
0.7921	Intermediate Similarity	NPD5281	Approved
0.7921	Intermediate Similarity	NPD5284	Approved
0.7909	Intermediate Similarity	NPD4634	Approved
0.79	Intermediate Similarity	NPD5328	Approved
0.789	Intermediate Similarity	NPD6881	Approved
0.789	Intermediate Similarity	NPD6899	Approved
0.789	Intermediate Similarity	NPD7320	Approved
0.7885	Intermediate Similarity	NPD4755	Approved
0.787	Intermediate Similarity	NPD6008	Approved
0.7838	Intermediate Similarity	NPD6649	Approved
0.7838	Intermediate Similarity	NPD6650	Approved
0.7798	Intermediate Similarity	NPD5697	Approved
0.7798	Intermediate Similarity	NPD5701	Approved
0.7768	Intermediate Similarity	NPD8297	Approved
0.7759	Intermediate Similarity	NPD6319	Approved
0.7755	Intermediate Similarity	NPD4786	Approved
0.7748	Intermediate Similarity	NPD7102	Approved
0.7748	Intermediate Similarity	NPD7290	Approved
0.7748	Intermediate Similarity	NPD6883	Approved
0.7745	Intermediate Similarity	NPD6079	Approved
0.7736	Intermediate Similarity	NPD4700	Approved
0.7736	Intermediate Similarity	NPD4696	Approved
0.7736	Intermediate Similarity	NPD5285	Approved
0.7736	Intermediate Similarity	NPD5286	Approved
0.7727	Intermediate Similarity	NPD6011	Approved
0.7679	Intermediate Similarity	NPD6617	Approved
0.7679	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD6847	Approved
0.7679	Intermediate Similarity	NPD6869	Approved
0.7679	Intermediate Similarity	NPD8130	Phase 1
0.767	Intermediate Similarity	NPD4202	Approved
0.7664	Intermediate Similarity	NPD5223	Approved
0.7658	Intermediate Similarity	NPD6012	Approved
0.7658	Intermediate Similarity	NPD6013	Approved
0.7658	Intermediate Similarity	NPD6014	Approved
0.7652	Intermediate Similarity	NPD6009	Approved
0.7619	Intermediate Similarity	NPD4697	Phase 3
0.7611	Intermediate Similarity	NPD6882	Approved
0.76	Intermediate Similarity	NPD3618	Phase 1
0.7593	Intermediate Similarity	NPD5224	Approved
0.7593	Intermediate Similarity	NPD5225	Approved
0.7593	Intermediate Similarity	NPD4633	Approved
0.7593	Intermediate Similarity	NPD5226	Approved
0.7593	Intermediate Similarity	NPD5211	Phase 2
0.7573	Intermediate Similarity	NPD6411	Approved
0.7551	Intermediate Similarity	NPD3667	Approved
0.7523	Intermediate Similarity	NPD5174	Approved
0.7523	Intermediate Similarity	NPD5175	Approved
0.7523	Intermediate Similarity	NPD4754	Approved
0.75	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD7638	Approved
0.7458	Intermediate Similarity	NPD6059	Approved
0.7458	Intermediate Similarity	NPD6054	Approved
0.7455	Intermediate Similarity	NPD5141	Approved
0.7453	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5222	Approved
0.7453	Intermediate Similarity	NPD5221	Approved
0.7438	Intermediate Similarity	NPD6616	Approved
0.7426	Intermediate Similarity	NPD5279	Phase 3
0.7417	Intermediate Similarity	NPD7604	Phase 2
0.7407	Intermediate Similarity	NPD7640	Approved
0.7407	Intermediate Similarity	NPD7639	Approved
0.7404	Intermediate Similarity	NPD8035	Phase 2
0.7404	Intermediate Similarity	NPD7515	Phase 2
0.7404	Intermediate Similarity	NPD8034	Phase 2
0.74	Intermediate Similarity	NPD3665	Phase 1
0.74	Intermediate Similarity	NPD3133	Approved
0.74	Intermediate Similarity	NPD3666	Approved
0.7395	Intermediate Similarity	NPD5983	Phase 2
0.7387	Intermediate Similarity	NPD4767	Approved
0.7387	Intermediate Similarity	NPD4768	Approved
0.7383	Intermediate Similarity	NPD5173	Approved
0.7383	Intermediate Similarity	NPD6084	Phase 2
0.7383	Intermediate Similarity	NPD6083	Phase 2
0.7379	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD6101	Approved
0.7377	Intermediate Similarity	NPD7078	Approved
0.7377	Intermediate Similarity	NPD8293	Discontinued
0.7358	Intermediate Similarity	NPD5695	Phase 3
0.7333	Intermediate Similarity	NPD5778	Approved
0.7333	Intermediate Similarity	NPD5779	Approved
0.7333	Intermediate Similarity	NPD6370	Approved
0.7321	Intermediate Similarity	NPD6412	Phase 2
0.7317	Intermediate Similarity	NPD7736	Approved
0.7295	Intermediate Similarity	NPD7507	Approved
0.7295	Intermediate Similarity	NPD6336	Discontinued
0.7288	Intermediate Similarity	NPD6335	Approved
0.7265	Intermediate Similarity	NPD6274	Approved
0.7257	Intermediate Similarity	NPD5128	Approved
0.7257	Intermediate Similarity	NPD4730	Approved
0.7257	Intermediate Similarity	NPD4729	Approved
0.7255	Intermediate Similarity	NPD4694	Approved
0.7255	Intermediate Similarity	NPD6409	Approved
0.7255	Intermediate Similarity	NPD7521	Approved
0.7255	Intermediate Similarity	NPD5330	Approved
0.7255	Intermediate Similarity	NPD6684	Approved
0.7255	Intermediate Similarity	NPD7146	Approved
0.7255	Intermediate Similarity	NPD7334	Approved
0.7255	Intermediate Similarity	NPD5280	Approved
0.725	Intermediate Similarity	NPD6015	Approved
0.725	Intermediate Similarity	NPD6016	Approved
0.7238	Intermediate Similarity	NPD6050	Approved
0.7227	Intermediate Similarity	NPD7101	Approved
0.7227	Intermediate Similarity	NPD7100	Approved
0.7222	Intermediate Similarity	NPD7902	Approved
0.7212	Intermediate Similarity	NPD4753	Phase 2
0.7203	Intermediate Similarity	NPD6317	Approved
0.7203	Intermediate Similarity	NPD7115	Discovery
0.7196	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5988	Approved
0.7172	Intermediate Similarity	NPD7525	Registered
0.7156	Intermediate Similarity	NPD5696	Approved
0.7155	Intermediate Similarity	NPD6053	Discontinued
0.7143	Intermediate Similarity	NPD6115	Approved
0.7143	Intermediate Similarity	NPD6314	Approved
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.7143	Intermediate Similarity	NPD6313	Approved
0.7143	Intermediate Similarity	NPD6697	Approved
0.7143	Intermediate Similarity	NPD5207	Approved
0.7143	Intermediate Similarity	NPD6118	Approved
0.7143	Intermediate Similarity	NPD6114	Approved
0.713	Intermediate Similarity	NPD5251	Approved
0.713	Intermediate Similarity	NPD5250	Approved
0.713	Intermediate Similarity	NPD5169	Approved
0.713	Intermediate Similarity	NPD5249	Phase 3
0.713	Intermediate Similarity	NPD5247	Approved
0.713	Intermediate Similarity	NPD5248	Approved
0.713	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5135	Approved
0.712	Intermediate Similarity	NPD7319	Approved
0.7115	Intermediate Similarity	NPD6903	Approved
0.7115	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6908	Approved
0.7107	Intermediate Similarity	NPD6909	Approved
0.7107	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD7748	Approved
0.7075	Intermediate Similarity	NPD5694	Approved
0.7069	Intermediate Similarity	NPD5215	Approved
0.7069	Intermediate Similarity	NPD5216	Approved
0.7069	Intermediate Similarity	NPD5127	Approved
0.7069	Intermediate Similarity	NPD5217	Approved
0.7059	Intermediate Similarity	NPD3668	Phase 3
0.7043	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6116	Phase 1
0.704	Intermediate Similarity	NPD6033	Approved
0.7037	Intermediate Similarity	NPD4629	Approved
0.7037	Intermediate Similarity	NPD5210	Approved
0.703	Intermediate Similarity	NPD4223	Phase 3
0.703	Intermediate Similarity	NPD4221	Approved
0.701	Intermediate Similarity	NPD6942	Approved
0.701	Intermediate Similarity	NPD7339	Approved
0.7	Intermediate Similarity	NPD5368	Approved
0.699	Remote Similarity	NPD5329	Approved
0.6975	Remote Similarity	NPD6868	Approved
0.6952	Remote Similarity	NPD5737	Approved
0.6952	Remote Similarity	NPD6672	Approved
0.6944	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7900	Approved
0.6939	Remote Similarity	NPD6117	Approved
0.6939	Remote Similarity	NPD6933	Approved
0.6923	Remote Similarity	NPD5690	Phase 2
0.6923	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6098	Approved
0.6917	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD7637	Suspended
0.6893	Remote Similarity	NPD4197	Approved
0.6891	Remote Similarity	NPD5167	Approved
0.6887	Remote Similarity	NPD6904	Approved
0.6887	Remote Similarity	NPD6080	Approved
0.6887	Remote Similarity	NPD6673	Approved
0.6887	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6435	Approved
0.6857	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD8328	Phase 3
0.6855	Remote Similarity	NPD6067	Discontinued
0.6832	Remote Similarity	NPD4748	Discontinued
0.6829	Remote Similarity	NPD7503	Approved
0.6822	Remote Similarity	NPD4096	Approved
0.6814	Remote Similarity	NPD7632	Discontinued
0.681	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.681	Remote Similarity	NPD5168	Approved
0.6796	Remote Similarity	NPD4788	Approved
0.6796	Remote Similarity	NPD5362	Discontinued
0.6792	Remote Similarity	NPD4518	Approved
0.6789	Remote Similarity	NPD6001	Approved
0.6765	Remote Similarity	NPD5369	Approved
0.6765	Remote Similarity	NPD4692	Approved
0.6765	Remote Similarity	NPD4139	Approved
0.6762	Remote Similarity	NPD5786	Approved
0.6762	Remote Similarity	NPD4690	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